金属催化的呋喃炔衍生物分子内环化及相关反应研究
|
摘要
呋喃是一种最简单的含氧五元杂环化合物。自1870年德国化学家成功合成以来,历经一百多年的发展,呋喃及其衍生物的合成已经实现了工业化、商品化。同时,呋喃及其衍生物也是一种重要的合成中间体,具有良好的反应活性,可作为双烯体与烯烃、炔烃、联烯等发生D-A反应；在酸性环境下可以发生开环反应得到二羰基类化合物；在过渡金属催化或者过氧化物存在下,也可以发生分子内或分子间的化学转化反应。本文的工作主要是利用了呋喃的这些特性,从简单原料呋喃出发,通过底物设计,合成出若干呋喃炔底物及呋喃醇衍生物,在不同金属催化下经过分子内、分子间的多步串联反应,完成一系列杂环及稠环化合物的合成方法学研究。主要包括以下四个部分：
1.发展了一种高效、立体选择性良好的合成萘酚烯酮类化合物的方法。在金催化作用下实现了分子内呋喃与炔烃的环化反应,合成了多取代的萘酚烯酮衍生物。该方法原料易得、条件温和、立体选择性好、普适性广,收率可达59%-99%。并且产物可通过脱硅、氧化反应一锅法转化为香豆素类衍生物。
2.第一部分研究工作表明萘酚烯酮衍生物的形成经历了芳构化过程。我们设想能否通过底物修饰,阻断其芳构化过程,探索呋喃炔环化的其他反应模式。将与呋喃环相连的碳原子由仲碳变为叔碳,切断萘酚衍生物的生成路线,探索其他的可能反应途径。实验证实,这种修饰过的呋喃炔底物在金催化下的确经历了不同的反应途径,发生了分子内呋喃、噻吩及吡咯的1,5-迁移反应,构筑了一系列的三取代烯烃类化合物。该反应模式比较新颖,值得我们深入研究。
3.探索了分子内呋喃与未活化炔烃的D-A反应,发展了一种高效合成氧杂桥环及蒽类化合物的方法。通过底物设计,用苯环作为桥连,将呋喃与炔丙醇碳酸酯构筑在同一个分子内。在硼酸及钯的共同作用下,炔丙醇碳酸酯与硼酸先形成联烯,进而与分子内的呋喃发生[4+2]反应,合成出一系列氧杂桥环化合物。该方法实现了分子内呋喃与未活化炔烃的D-A反应,原料易得,条件温和,普适性广。并且产物在三氟化硼乙醚催化下几乎可以定量收率转化成蒽类化合物。
4.建立了一种环戊酮并吡咯酮类衍生物的高效合成方法。在路易斯酸催化下,呋喃醇与烯胺酮发生分子间反应,选择性的实现了烯胺酮α-碳对呋喃衍生物的5-位发生亲核进攻反应。进而经过C-O键断裂、4π电环化过程,发生分子内氮原子对烯酮的迈克尔加成反应,合成出环戊酮并吡咯酮衍生物。该方法反应条件温和,化学选择性单一,普适性良好,收率为53%-94%。而且产物的类似物具有抗心脑血管的药用价值。
通过上述方法,合成出17个萘酚烯酮衍生物,1个香豆素化合物,18个杂环迁移产物,2个吲哚并环化合物,14个氧杂桥环化合物,5个蒽类化合物,16个环戊酮并吡咯酮类化合物。新化合物均通过了1H NMR,13C NMR及质谱进行表征。
Furans are important synthetic intermediates. They can participate in a variety of reactions such as Diels-Alder reaction, oxidation reaction and ring-opening reaction. This thesis is focused on the development of novel synthetic methodologies of heterocyclic compounds or polycyclic compounds based on the intramolecular or intermolecular reactions of furans using furan/ynes as starting materials. It includes the following four parts:
1. Gold(Ⅰ)-catalyzed intramolecular cyclo-isomerization of furan/ynes bearing a silyloxy or allyloxy group has been developed, which provides a highly efficient access to protected1-naphthol derivatives with enal or enone moiety. The method offers several advantages such as high stereoselectivities, mild reaction conditions, and easily accessible starting materials. In addition, the naphthyl products could be further transformed into the important benzocoumarins in a one-pot procedure.
2. Gold(Ⅰ)-catalyzed cycloisomerizations of1,4-furan/ynes afforded an efficient and stereoselective access to trisubstituted alkenes under mild reaction conditions. The reaction likely proceeds via cascade cyclization/Grob-type fragmentation with concomitant1,5-migration of furanyl group. In addition to furan rings, other heterocycles such as benzofurans, thiophenes and pyrroles underwent1,5-migrations equally well.
3. A highly efficient palladium-catalyzed cascade reactions of propargyl carbonates bearing a furanyl group with organoborons has been developed. This methodology offers rapid access to polycyclic Diels-Alder cycloadducts in good to high yields. The thus formed oxygen-bridged products could be further converted to anthracene derivatives in a chemoselective manner under mild conditions.
4. A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo-and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields. The resulting azabicyclic compounds are important azacarboprostacyclin analogs, which are potentially useful in the treatment of thrombotic disease.
1.发展了一种高效、立体选择性良好的合成萘酚烯酮类化合物的方法。在金催化作用下实现了分子内呋喃与炔烃的环化反应,合成了多取代的萘酚烯酮衍生物。该方法原料易得、条件温和、立体选择性好、普适性广,收率可达59%-99%。并且产物可通过脱硅、氧化反应一锅法转化为香豆素类衍生物。
2.第一部分研究工作表明萘酚烯酮衍生物的形成经历了芳构化过程。我们设想能否通过底物修饰,阻断其芳构化过程,探索呋喃炔环化的其他反应模式。将与呋喃环相连的碳原子由仲碳变为叔碳,切断萘酚衍生物的生成路线,探索其他的可能反应途径。实验证实,这种修饰过的呋喃炔底物在金催化下的确经历了不同的反应途径,发生了分子内呋喃、噻吩及吡咯的1,5-迁移反应,构筑了一系列的三取代烯烃类化合物。该反应模式比较新颖,值得我们深入研究。
3.探索了分子内呋喃与未活化炔烃的D-A反应,发展了一种高效合成氧杂桥环及蒽类化合物的方法。通过底物设计,用苯环作为桥连,将呋喃与炔丙醇碳酸酯构筑在同一个分子内。在硼酸及钯的共同作用下,炔丙醇碳酸酯与硼酸先形成联烯,进而与分子内的呋喃发生[4+2]反应,合成出一系列氧杂桥环化合物。该方法实现了分子内呋喃与未活化炔烃的D-A反应,原料易得,条件温和,普适性广。并且产物在三氟化硼乙醚催化下几乎可以定量收率转化成蒽类化合物。
4.建立了一种环戊酮并吡咯酮类衍生物的高效合成方法。在路易斯酸催化下,呋喃醇与烯胺酮发生分子间反应,选择性的实现了烯胺酮α-碳对呋喃衍生物的5-位发生亲核进攻反应。进而经过C-O键断裂、4π电环化过程,发生分子内氮原子对烯酮的迈克尔加成反应,合成出环戊酮并吡咯酮衍生物。该方法反应条件温和,化学选择性单一,普适性良好,收率为53%-94%。而且产物的类似物具有抗心脑血管的药用价值。
通过上述方法,合成出17个萘酚烯酮衍生物,1个香豆素化合物,18个杂环迁移产物,2个吲哚并环化合物,14个氧杂桥环化合物,5个蒽类化合物,16个环戊酮并吡咯酮类化合物。新化合物均通过了1H NMR,13C NMR及质谱进行表征。
Furans are important synthetic intermediates. They can participate in a variety of reactions such as Diels-Alder reaction, oxidation reaction and ring-opening reaction. This thesis is focused on the development of novel synthetic methodologies of heterocyclic compounds or polycyclic compounds based on the intramolecular or intermolecular reactions of furans using furan/ynes as starting materials. It includes the following four parts:
1. Gold(Ⅰ)-catalyzed intramolecular cyclo-isomerization of furan/ynes bearing a silyloxy or allyloxy group has been developed, which provides a highly efficient access to protected1-naphthol derivatives with enal or enone moiety. The method offers several advantages such as high stereoselectivities, mild reaction conditions, and easily accessible starting materials. In addition, the naphthyl products could be further transformed into the important benzocoumarins in a one-pot procedure.
2. Gold(Ⅰ)-catalyzed cycloisomerizations of1,4-furan/ynes afforded an efficient and stereoselective access to trisubstituted alkenes under mild reaction conditions. The reaction likely proceeds via cascade cyclization/Grob-type fragmentation with concomitant1,5-migration of furanyl group. In addition to furan rings, other heterocycles such as benzofurans, thiophenes and pyrroles underwent1,5-migrations equally well.
3. A highly efficient palladium-catalyzed cascade reactions of propargyl carbonates bearing a furanyl group with organoborons has been developed. This methodology offers rapid access to polycyclic Diels-Alder cycloadducts in good to high yields. The thus formed oxygen-bridged products could be further converted to anthracene derivatives in a chemoselective manner under mild conditions.
4. A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo-and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields. The resulting azabicyclic compounds are important azacarboprostacyclin analogs, which are potentially useful in the treatment of thrombotic disease.
引文
1. H. Limpricht, Ber. Dtsch. Chem. Ges.1870, 3,90-91
2. (a) Bourne, Richard A.; Poliakoff, Martyn; Stevens, James G.; Twigg, Martyn V. Angew. Chem., Int. Ed, 2010,49,8856-8859. (b) Capote, Armand J.; Madix, Robert J.; Roberts, Jeffrey T. J. Am. Chem. Soc.,1991,113,9848-9851.
3. Feist. F. Chem. Ber. 1902,35,1545
4. Benary, E. Ber,1911,44,489-493.
5. Raghavan, S. Anuradha, K. Synlett, 2003,711
6. Mineto. G.; Raveglia, L. F.; Taddel, M. Org. Lett, 2004,6,389
7. (a) Knorr, L. Ber.1884,17,2863-2870. (b) Paal, C. Ber.1884,17,2756-2767.
8. (a) Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem.,2002, 67,2653 (b) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc.,2004,126,11164; (c) Patil, N. T.; Yamamoto, Y. J. Org. Chem.,2004,69,5139; (d) Patil, N. T.; Wu, N. T.; Yamamoto, Y. J. Org. Chem.,2005,70,4531; (e) Oh, C. H.; Reddy, V. R.; Kim, A.; Rhim, C. Y. Tetrahedron Lett.,2006,47,5307; (f) Du, X.; Chen, H.; Liu, Y. Chem.-Eur. J.,2008,14,9495; (g) Du, X.; Chen, H.; Chen, Y.; Chen, J.; Liu, Y. Synlett, 2011,1010.
9. (a) Du, X.; Song, F.; Lu, Y.; Chen, H.; Liu, Y. Tetrahedron, 2009,65,1839; (b) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett.,2005,7,5409; (c) Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Eur. J. Org. Chem.,2011,667. (d) Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Chem.-Eur. J., 2011,17,8195;
10.(a)Schwier, T.;Sromek, A.W.,Yap, D.M.L.；Chernyak, D.；Gevorgyan, V.J. Am. Chem. Soc.,2007, 29,9868；(b)Dudnik, A.S.；Sromek,A.W.；Rubina, M.； Kim, J.T.；Kel'in, A. V.; Gevorgyan, V. J. Am.Chem. Soc.,2008,130,1440.
11.(a)Wakabayashi, Y.；Fukuda, Y.；Shiragami,H.；Utimoto, K.；Nozaki, H. Tetrahedron, 1985,41, 3655.(b)Gabriele, B.；Salerno, G.；Lauria,E. J. Org. Chem.,1999,64,7687;
12.MaGee, D.I.；Leach, J.D.；Setiadji, S.Tetrahedron, 1999,55,2847.
13.(a)Wipf P.；Rahman, L.T.; Rector, S.R.J. Org. Chem.,1998, 63,7132.(b)Liu, F.；Qian,D.; Li, L.；Zhao,X.; Zhang, J. Angew. Chem.,Int. Ed.,2010, 49,6669；
14.(a)Marshall, J.A.；Robinson, E.D.J. Org: Chem.,1990, 55,3450；(b)Marshall, J. A.；Wang, X.-J.; J. Org. Chem.,1991,56, 960; (c)Marshall, J.A.；Wallace, E.M.； Coan, P.S.J. Org. Chem.,1995,60, 796; (d)Hashmi, A.S.K.; Sehon, C.A.J. Org. Chem.,1995,60,5966；(e)Hashmi, A.S.K.；Ruppert, T.L.；Knofel, T. Bats, J.W.J. Org. Chem.,1998,62,7295; (f)Hashmi,A.S.K.；Choi, J.-H.；Bats, J.W.J. Prakt. Chem.,1999,341,342; (g)Hashmi, A.S.K.；Frost, T.M.；Bats, J. W.J. Am. Chem. Soc.,2000,, 22,11553-11554. (h)Hashmi,A.S.K.; Schwarz, L.；Bolte, M.Eur., J. Org. Chem.,2004,1923；(i)Hashmi, A.S.K.; Blanco, M.C.； Fischer, D.；Bats, J.W.Eur.J. Org. Chem.,2006,1387；
15.Sera, A.；Ohara, M.；Kubo, T.；Itoh, K.；Yamada, H.；Mikata, Y.; Org. Chem. 1988, 53,5460-5464
16.Ruli's ek, L.;S ebek, P；Havlas, Z.；Hrabal,R.; C.apek,P.; Svatos, A.; J. Org. Chem. 2005,70,6295-6302
17. Li, C. C.；Liang, S.；Zhang, X.H.; Xie, Z.X.；Chen, J.H.；Wu, Y D.; Yang, Z.; Org. Lett. 2005,7,3709-3712.
18.Fang, L.C.；Chen, Y.；Huang, J.；Liu, Z.L.；Quan, J.M.；Li, C.C.；Yang, Z.; J. Org. Chem.,2011,76,2479-2487
19. Chen, C.H.; Yellol, G.S.; Tsai, C.H.; Dalvi, P.B.; Sun, C.M.; J. Org. Chem. 2013,78,9738-9747
20. Piancatelli, A. Saarbadoro. Tetrhedron Letters,1976,39,3555-3558
21. Lai, J. Q. Eur. Org. Chem. 2009,2695-2699
22. Alaniz, R. D. Angew. Chem. Int. Ed. 2010,49,9484-9487
23. Alaniz, R. D. Angew. chem. Int. Ed. 2011,50,7167-7170
24. Yin, B. L.; Lai, J. Q.; Zhang, Z. R.; Jiang, H. F. Adv. Synth. Catal. 2011,353, 1961.
25. Alder, K. et al. Justus Liebigs Annalen der Chemie, 1960,638,187-198
26. Georgiadis, M. P.; Couladouros, E. J. Org. Chem,1986,51,2725 2727
27. Kelly, A. R.; Kerrigan, M. H.; Walsh, P. G J. Am. Chem. Soc. 2008,130, 4097-4104
28. Graziano, M. L.; Iesce, M. R. Synthesis,1985,12,1151-1153
29. Maurizio, D.; Rocco, R; Gianfranco, R. Eur. J. Org. Chem, 2000,19,3265-3272
30. Christopher F, A.; Christian, E.; Christopher R. H, H.; Nicolaou; Christian, N.; Derek, R.; Christopher F, A.; Christian, E.; Christopher R. H, H.; Nicolaou; Christian, N.; Derek, R. Angew. Chem. Int. Ed, 2012,51,4726-4730
31. Yin, B. L.; Cai, C. B.; Zeng, G. H.; Zhang, R. Q.; Li, X.; Jiang, H. F. Org. Lett. 2012,14,1098-1101
32. Yin, B. L.; Zeng, G. H.; Cai, C. B.; Ji, F. H.; Huang, L.; Li, Z. R.; Jiang, H. F. Org. Lett. 2012,14,616-619.
33. Hashmi, A. S. K.; Frost, T. J. M.; Bats, J. W. J. Am. Chem. Soc. 2000,122, 11553-11554.
34. Hashmi, A. S. K.; Frost, T. J. M.; Bats, J. W. Org. Lett.2001,3,3769-3771.
35. Wolfgang, F; Hashmi, A. S. K.; Woelfle, M.; Teles, J.; Henrique. Synlett, 2007,11, 1747-1752.
36. Hashmi, A. S. K.; Rominger, F.; Yang, W. B. Angew. Chem. Int. Ed,2011,50, 5762-5765.
37. Chen, Y. F.; Lu, Y. H.; Li, G. J.; Liu, Y. H, Org. Lett.2009,11,3838-3841.
38. Chen, Y. F.; Li, G. J.; Liu, Y. H, Adv. Synth. Catal. 2011,353,392-400.
39. Chen, Y. F.; Liu, Y. H, J. Org. Chem.,2011,76,5274-5282.
1.Son, J.K.;Jung, S.J.;Jung, J.H.;Fang, Z.; Lee, C.S.; Seo, C.S.; Moon, D.C.; Min, B.S.; Kim, M.R.; Woo, M. H. Chem. Pharm. Bull. 2008,56,213.
2.Itokawa, H.; Mihara, K.; Takeya, K.Chem.Pharm. Bull. 1983,31,2353.
3.Itokawa, H.; Ibraheim, Z.Z.；Qiao, Y.-F.; Takeya, K. Chem. Pharm. Bull. 1993,41, 1869.
4.Bringmann, G.; Messer, K.; Wolf, K.; Mu口hlbacher, J.; Gru口ne, M.; Brun, R.； Louis, A. M.Hytochemistry, 2002,60,389.
5.Boonsri, S.; Karalai, C.; Ponglimanont, C.; Chantrapromma, S.; Kanjana-opas, A. J. Nat.Prod. 2008,71,1173.
6.Rinehart, K.L.Jr. Acc Chem. Res.1972,5,57.
7.Chen,C..; Martin, S.F.J. Org. Chem. 2006,71,4810-4817
8.Akai,S.J.; Ikawa, T.；Takayanagi, S,I.；Morikawa,Y.；Mohri, S.;, Tsubakiyama, M.； Egi, M.；Wada, Y.; Kita, Y. Angew. Chem. Int. Ed. 2008,47,7673-7676
9.Ballantine, M.; Menard, M.; Tam, W. J. Org. Chem. 2009,74,7570-7573.
10.Hirokazu Tsukamoto and Yoshinori Kondo.Org. Lett. 2007,9, 4227-4230
11.Xu, H.; Li, S.F.; Liu, H.X.；Fu, H.；Jiang. Y.Y. Chem. commun.,2010,46,7617-7619
12.Huang, X.; Xue. J.; J. Org. Chem. 2007,72,3965-3968.
13.Chai,G. B.; Lu, Z.; Fu,C. L.；Ma. S. M. Chem. Eur. J. 2009,15,11083-11086
14.Sergeev, A.G; Schulz, T.; Torborg, C.；Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed. 2009,48,7595-7599.
15.Furukawa; Ijichi；Morimoto; Nogami；Chem. Pharm.Bull,1993,41,968-970
1. a) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron, 1997,53,14179; b) Harwood, L. M.; Brickwood, A. C.; Morrison, V.; Robertson, J.; Swallow, S. J. Heterocycl. Chem. 1999,36,1391; c) Keay, B. A.; Hunt, I. R. Adv. Cycloaddit. 1999,6,173.
2. Padwa, A.; Wang, Q. J. Org. Chem. 2006,71,3210-3220
3. Petronijevic, F.; Timmons, C.; Cuzzupey, A.; Wipf, P.; Chem. Commun., 2009, 104-106
4. Olaia, N. G.; Alonso, R. J. Org. Chem. 2013,78,2564-2570
5. LaPorte, M.; Hong, K. B.; Xu, J.; Wipf, P. J. Org. Chem. 2012,78,167;
6. Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999,64, 3595.
7. Chen, Y. F.; Wang, L.; Liu, Y. H.; Li, Y. X. Chem. Eur. J. 2011,17,12582-12586
8. Jung, M. E.; Min, S. J. J. Am. Chem. Soc.2005,127,10834-10835
9. Tsuji, T.; Watanake, M; Minami, M.; Shimizu, I. J. Am. Chem. Soc.1985,107, 2196
10. (a) Ruitenberg, K.; Kleijin, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981,22,1451 (b) Luong, T.; Linstrumelle, G. Tetrahedron Lett. 1980,21,5019 (c) For Ni-catalyzed related coupling, see: Wenkert, E.; Leftin, M. H.; Michelotti, E. L. J. Org. Chem. 1985,50,1122 (d) Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983,48,1103
11. a) Yoshida, M.; Higuchi, K.; Shishido, Org. Lett.2009,11,4752.b) Yan, W.; Wang, Q.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett.2010,12,3308;
1. Greenhill, J. V. Chem. Soc. Rev. 1997,277
2. (a) Martin, D. F.; Janusonis, G. A.; Martin, B. B. J. Am. Chem. Soc. 1961,83,73; (b) Palimkar, S. S.; More, V. S.; Srinivasan, K. V. Synth. Common. 2008,38,1456 (c) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008,10,2629
3. Braibante, H. T. S.; Braibante, M.E.F.; Rosso, G. B. J. Braz. Chem. Soc. 2003,14, 994.
4. Gholap, A. R.; Charor, N. S.; Daniel, T. J. Mol. Catal. A:Chem. 2006,245:37
5. Datta, B.; Reddy, M. B. M; Pasha, M. A. Synthetic Common. 2011,41,2331.
6. Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. synthesis, 1990,215
7. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y. Z. Eur. J. Org. Chem. 2010,4189
8. Xu, X. L.; Du, P.; Cheng, D. P.; Wang, H.; Li, X. N. Chem. Commun. 2012,48, 1811
9. For reviews, see: (a) Negri, G.; Kascheres, C.; Kascheres, A. J. J. Hetero cycl. Chem..2004,41,461; (b) Elassar, A. A.; El-Khair, A. A. Tetrahedron,2003,59, 8463
10. Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem. Int. Ed. 2010,49,7790-7794
11. Shao, Y. S.; Yao, W. J.; Liu, J.; Zhu, K.; Li, Y. Z. synthesis, 2012,44,3301-3306
12. Vohra, R. K.; Bruneau, C.; Renaud, J. L. Adv. Synth. Catal. 2006,348,2571
13. Palmieri, A.; Gabrielli, S.; Cimarelli, C.; Ballini, R. Green Chem.,2011,13, 3333-3336
14. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y Z. Eur. J. Org. Chem. 2010, 4189-4193
15. Xiang, D. X.; Xin, X. Q.; Liu, X.; Kumar, S.; Dong, D. W. Synlett. 2011,15,2187
16. WEN, L. R.; Wang, S. W.; Li, M.; Yang, H. Z.; Chinese Journal of Chemistry, 2005,23,1231-1235
17. Wang, X.; Turunen, B. J.; Leighty, M. W.; Georg, G. I. Tetrahedron Lett, 2007,48, 8811-8814.
18. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y. Z. Org. Biomol. Chem.,2011,9, 1342-1346
19. Ge, H. B.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008,130,3708-3709
20. Li, M. Z.; Li, L. X.; Ge, H. B. Adv. Synth. Catal. 2010,352,2445-2449
21. Chen, F.; Feng, Z.; He, C. Y.; Wang, H. Y.; Guo, Y. L.; Zhang, X. G.; Org. Lett, 2012,14,1176-1179
22.Wurtz,S.；Rakshit, S.；Neumann,J.J.；Droge, T.; Dlorius, F. Angew. Chem. Int. Ed. 2008,47,7230
23.Bernini, R.；Fabrizi, G.; Sferrazza, A.；Cacchi, S. Angew. Chem. Int. Ed. 2009,48, 8078
24. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009,11,2417
25.Ban, X.; Pan, Y.; Lin, Y. F.; Wang, S.Q.; Du, Y. F.；Zhao, K. Org. Biomol. Chem. 2012,10,3606
26. Guan, Z.H.; Yan, Z.Y.; Ren, Z.K.; Liu, X.Y.; Liang, Y. M. Chem. Commun., 2010,46,2823-2825
2. (a) Bourne, Richard A.; Poliakoff, Martyn; Stevens, James G.; Twigg, Martyn V. Angew. Chem., Int. Ed, 2010,49,8856-8859. (b) Capote, Armand J.; Madix, Robert J.; Roberts, Jeffrey T. J. Am. Chem. Soc.,1991,113,9848-9851.
3. Feist. F. Chem. Ber. 1902,35,1545
4. Benary, E. Ber,1911,44,489-493.
5. Raghavan, S. Anuradha, K. Synlett, 2003,711
6. Mineto. G.; Raveglia, L. F.; Taddel, M. Org. Lett, 2004,6,389
7. (a) Knorr, L. Ber.1884,17,2863-2870. (b) Paal, C. Ber.1884,17,2756-2767.
8. (a) Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem.,2002, 67,2653 (b) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc.,2004,126,11164; (c) Patil, N. T.; Yamamoto, Y. J. Org. Chem.,2004,69,5139; (d) Patil, N. T.; Wu, N. T.; Yamamoto, Y. J. Org. Chem.,2005,70,4531; (e) Oh, C. H.; Reddy, V. R.; Kim, A.; Rhim, C. Y. Tetrahedron Lett.,2006,47,5307; (f) Du, X.; Chen, H.; Liu, Y. Chem.-Eur. J.,2008,14,9495; (g) Du, X.; Chen, H.; Chen, Y.; Chen, J.; Liu, Y. Synlett, 2011,1010.
9. (a) Du, X.; Song, F.; Lu, Y.; Chen, H.; Liu, Y. Tetrahedron, 2009,65,1839; (b) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett.,2005,7,5409; (c) Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Eur. J. Org. Chem.,2011,667. (d) Hashmi, A. S. K.; Haffner, T.; Rudolph, M.; Rominger, F. Chem.-Eur. J., 2011,17,8195;
10.(a)Schwier, T.;Sromek, A.W.,Yap, D.M.L.；Chernyak, D.；Gevorgyan, V.J. Am. Chem. Soc.,2007, 29,9868；(b)Dudnik, A.S.；Sromek,A.W.；Rubina, M.； Kim, J.T.；Kel'in, A. V.; Gevorgyan, V. J. Am.Chem. Soc.,2008,130,1440.
11.(a)Wakabayashi, Y.；Fukuda, Y.；Shiragami,H.；Utimoto, K.；Nozaki, H. Tetrahedron, 1985,41, 3655.(b)Gabriele, B.；Salerno, G.；Lauria,E. J. Org. Chem.,1999,64,7687;
12.MaGee, D.I.；Leach, J.D.；Setiadji, S.Tetrahedron, 1999,55,2847.
13.(a)Wipf P.；Rahman, L.T.; Rector, S.R.J. Org. Chem.,1998, 63,7132.(b)Liu, F.；Qian,D.; Li, L.；Zhao,X.; Zhang, J. Angew. Chem.,Int. Ed.,2010, 49,6669；
14.(a)Marshall, J.A.；Robinson, E.D.J. Org: Chem.,1990, 55,3450；(b)Marshall, J. A.；Wang, X.-J.; J. Org. Chem.,1991,56, 960; (c)Marshall, J.A.；Wallace, E.M.； Coan, P.S.J. Org. Chem.,1995,60, 796; (d)Hashmi, A.S.K.; Sehon, C.A.J. Org. Chem.,1995,60,5966；(e)Hashmi, A.S.K.；Ruppert, T.L.；Knofel, T. Bats, J.W.J. Org. Chem.,1998,62,7295; (f)Hashmi,A.S.K.；Choi, J.-H.；Bats, J.W.J. Prakt. Chem.,1999,341,342; (g)Hashmi, A.S.K.；Frost, T.M.；Bats, J. W.J. Am. Chem. Soc.,2000,, 22,11553-11554. (h)Hashmi,A.S.K.; Schwarz, L.；Bolte, M.Eur., J. Org. Chem.,2004,1923；(i)Hashmi, A.S.K.; Blanco, M.C.； Fischer, D.；Bats, J.W.Eur.J. Org. Chem.,2006,1387；
15.Sera, A.；Ohara, M.；Kubo, T.；Itoh, K.；Yamada, H.；Mikata, Y.; Org. Chem. 1988, 53,5460-5464
16.Ruli's ek, L.;S ebek, P；Havlas, Z.；Hrabal,R.; C.apek,P.; Svatos, A.; J. Org. Chem. 2005,70,6295-6302
17. Li, C. C.；Liang, S.；Zhang, X.H.; Xie, Z.X.；Chen, J.H.；Wu, Y D.; Yang, Z.; Org. Lett. 2005,7,3709-3712.
18.Fang, L.C.；Chen, Y.；Huang, J.；Liu, Z.L.；Quan, J.M.；Li, C.C.；Yang, Z.; J. Org. Chem.,2011,76,2479-2487
19. Chen, C.H.; Yellol, G.S.; Tsai, C.H.; Dalvi, P.B.; Sun, C.M.; J. Org. Chem. 2013,78,9738-9747
20. Piancatelli, A. Saarbadoro. Tetrhedron Letters,1976,39,3555-3558
21. Lai, J. Q. Eur. Org. Chem. 2009,2695-2699
22. Alaniz, R. D. Angew. Chem. Int. Ed. 2010,49,9484-9487
23. Alaniz, R. D. Angew. chem. Int. Ed. 2011,50,7167-7170
24. Yin, B. L.; Lai, J. Q.; Zhang, Z. R.; Jiang, H. F. Adv. Synth. Catal. 2011,353, 1961.
25. Alder, K. et al. Justus Liebigs Annalen der Chemie, 1960,638,187-198
26. Georgiadis, M. P.; Couladouros, E. J. Org. Chem,1986,51,2725 2727
27. Kelly, A. R.; Kerrigan, M. H.; Walsh, P. G J. Am. Chem. Soc. 2008,130, 4097-4104
28. Graziano, M. L.; Iesce, M. R. Synthesis,1985,12,1151-1153
29. Maurizio, D.; Rocco, R; Gianfranco, R. Eur. J. Org. Chem, 2000,19,3265-3272
30. Christopher F, A.; Christian, E.; Christopher R. H, H.; Nicolaou; Christian, N.; Derek, R.; Christopher F, A.; Christian, E.; Christopher R. H, H.; Nicolaou; Christian, N.; Derek, R. Angew. Chem. Int. Ed, 2012,51,4726-4730
31. Yin, B. L.; Cai, C. B.; Zeng, G. H.; Zhang, R. Q.; Li, X.; Jiang, H. F. Org. Lett. 2012,14,1098-1101
32. Yin, B. L.; Zeng, G. H.; Cai, C. B.; Ji, F. H.; Huang, L.; Li, Z. R.; Jiang, H. F. Org. Lett. 2012,14,616-619.
33. Hashmi, A. S. K.; Frost, T. J. M.; Bats, J. W. J. Am. Chem. Soc. 2000,122, 11553-11554.
34. Hashmi, A. S. K.; Frost, T. J. M.; Bats, J. W. Org. Lett.2001,3,3769-3771.
35. Wolfgang, F; Hashmi, A. S. K.; Woelfle, M.; Teles, J.; Henrique. Synlett, 2007,11, 1747-1752.
36. Hashmi, A. S. K.; Rominger, F.; Yang, W. B. Angew. Chem. Int. Ed,2011,50, 5762-5765.
37. Chen, Y. F.; Lu, Y. H.; Li, G. J.; Liu, Y. H, Org. Lett.2009,11,3838-3841.
38. Chen, Y. F.; Li, G. J.; Liu, Y. H, Adv. Synth. Catal. 2011,353,392-400.
39. Chen, Y. F.; Liu, Y. H, J. Org. Chem.,2011,76,5274-5282.
1.Son, J.K.;Jung, S.J.;Jung, J.H.;Fang, Z.; Lee, C.S.; Seo, C.S.; Moon, D.C.; Min, B.S.; Kim, M.R.; Woo, M. H. Chem. Pharm. Bull. 2008,56,213.
2.Itokawa, H.; Mihara, K.; Takeya, K.Chem.Pharm. Bull. 1983,31,2353.
3.Itokawa, H.; Ibraheim, Z.Z.；Qiao, Y.-F.; Takeya, K. Chem. Pharm. Bull. 1993,41, 1869.
4.Bringmann, G.; Messer, K.; Wolf, K.; Mu口hlbacher, J.; Gru口ne, M.; Brun, R.； Louis, A. M.Hytochemistry, 2002,60,389.
5.Boonsri, S.; Karalai, C.; Ponglimanont, C.; Chantrapromma, S.; Kanjana-opas, A. J. Nat.Prod. 2008,71,1173.
6.Rinehart, K.L.Jr. Acc Chem. Res.1972,5,57.
7.Chen,C..; Martin, S.F.J. Org. Chem. 2006,71,4810-4817
8.Akai,S.J.; Ikawa, T.；Takayanagi, S,I.；Morikawa,Y.；Mohri, S.;, Tsubakiyama, M.； Egi, M.；Wada, Y.; Kita, Y. Angew. Chem. Int. Ed. 2008,47,7673-7676
9.Ballantine, M.; Menard, M.; Tam, W. J. Org. Chem. 2009,74,7570-7573.
10.Hirokazu Tsukamoto and Yoshinori Kondo.Org. Lett. 2007,9, 4227-4230
11.Xu, H.; Li, S.F.; Liu, H.X.；Fu, H.；Jiang. Y.Y. Chem. commun.,2010,46,7617-7619
12.Huang, X.; Xue. J.; J. Org. Chem. 2007,72,3965-3968.
13.Chai,G. B.; Lu, Z.; Fu,C. L.；Ma. S. M. Chem. Eur. J. 2009,15,11083-11086
14.Sergeev, A.G; Schulz, T.; Torborg, C.；Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem. Int. Ed. 2009,48,7595-7599.
15.Furukawa; Ijichi；Morimoto; Nogami；Chem. Pharm.Bull,1993,41,968-970
1. a) Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron, 1997,53,14179; b) Harwood, L. M.; Brickwood, A. C.; Morrison, V.; Robertson, J.; Swallow, S. J. Heterocycl. Chem. 1999,36,1391; c) Keay, B. A.; Hunt, I. R. Adv. Cycloaddit. 1999,6,173.
2. Padwa, A.; Wang, Q. J. Org. Chem. 2006,71,3210-3220
3. Petronijevic, F.; Timmons, C.; Cuzzupey, A.; Wipf, P.; Chem. Commun., 2009, 104-106
4. Olaia, N. G.; Alonso, R. J. Org. Chem. 2013,78,2564-2570
5. LaPorte, M.; Hong, K. B.; Xu, J.; Wipf, P. J. Org. Chem. 2012,78,167;
6. Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999,64, 3595.
7. Chen, Y. F.; Wang, L.; Liu, Y. H.; Li, Y. X. Chem. Eur. J. 2011,17,12582-12586
8. Jung, M. E.; Min, S. J. J. Am. Chem. Soc.2005,127,10834-10835
9. Tsuji, T.; Watanake, M; Minami, M.; Shimizu, I. J. Am. Chem. Soc.1985,107, 2196
10. (a) Ruitenberg, K.; Kleijin, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981,22,1451 (b) Luong, T.; Linstrumelle, G. Tetrahedron Lett. 1980,21,5019 (c) For Ni-catalyzed related coupling, see: Wenkert, E.; Leftin, M. H.; Michelotti, E. L. J. Org. Chem. 1985,50,1122 (d) Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983,48,1103
11. a) Yoshida, M.; Higuchi, K.; Shishido, Org. Lett.2009,11,4752.b) Yan, W.; Wang, Q.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett.2010,12,3308;
1. Greenhill, J. V. Chem. Soc. Rev. 1997,277
2. (a) Martin, D. F.; Janusonis, G. A.; Martin, B. B. J. Am. Chem. Soc. 1961,83,73; (b) Palimkar, S. S.; More, V. S.; Srinivasan, K. V. Synth. Common. 2008,38,1456 (c) Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008,10,2629
3. Braibante, H. T. S.; Braibante, M.E.F.; Rosso, G. B. J. Braz. Chem. Soc. 2003,14, 994.
4. Gholap, A. R.; Charor, N. S.; Daniel, T. J. Mol. Catal. A:Chem. 2006,245:37
5. Datta, B.; Reddy, M. B. M; Pasha, M. A. Synthetic Common. 2011,41,2331.
6. Sakamoto, T.; Nagano, T.; Kondo, Y.; Yamanaka, H. synthesis, 1990,215
7. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y. Z. Eur. J. Org. Chem. 2010,4189
8. Xu, X. L.; Du, P.; Cheng, D. P.; Wang, H.; Li, X. N. Chem. Commun. 2012,48, 1811
9. For reviews, see: (a) Negri, G.; Kascheres, C.; Kascheres, A. J. J. Hetero cycl. Chem..2004,41,461; (b) Elassar, A. A.; El-Khair, A. A. Tetrahedron,2003,59, 8463
10. Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem. Int. Ed. 2010,49,7790-7794
11. Shao, Y. S.; Yao, W. J.; Liu, J.; Zhu, K.; Li, Y. Z. synthesis, 2012,44,3301-3306
12. Vohra, R. K.; Bruneau, C.; Renaud, J. L. Adv. Synth. Catal. 2006,348,2571
13. Palmieri, A.; Gabrielli, S.; Cimarelli, C.; Ballini, R. Green Chem.,2011,13, 3333-3336
14. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y Z. Eur. J. Org. Chem. 2010, 4189-4193
15. Xiang, D. X.; Xin, X. Q.; Liu, X.; Kumar, S.; Dong, D. W. Synlett. 2011,15,2187
16. WEN, L. R.; Wang, S. W.; Li, M.; Yang, H. Z.; Chinese Journal of Chemistry, 2005,23,1231-1235
17. Wang, X.; Turunen, B. J.; Leighty, M. W.; Georg, G. I. Tetrahedron Lett, 2007,48, 8811-8814.
18. Yang, J. Y.; Wang, C. Y.; Xie, X.; Li, H. F.; Li, Y. Z. Org. Biomol. Chem.,2011,9, 1342-1346
19. Ge, H. B.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008,130,3708-3709
20. Li, M. Z.; Li, L. X.; Ge, H. B. Adv. Synth. Catal. 2010,352,2445-2449
21. Chen, F.; Feng, Z.; He, C. Y.; Wang, H. Y.; Guo, Y. L.; Zhang, X. G.; Org. Lett, 2012,14,1176-1179
22.Wurtz,S.；Rakshit, S.；Neumann,J.J.；Droge, T.; Dlorius, F. Angew. Chem. Int. Ed. 2008,47,7230
23.Bernini, R.；Fabrizi, G.; Sferrazza, A.；Cacchi, S. Angew. Chem. Int. Ed. 2009,48, 8078
24. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009,11,2417
25.Ban, X.; Pan, Y.; Lin, Y. F.; Wang, S.Q.; Du, Y. F.；Zhao, K. Org. Biomol. Chem. 2012,10,3606
26. Guan, Z.H.; Yan, Z.Y.; Ren, Z.K.; Liu, X.Y.; Liang, Y. M. Chem. Commun., 2010,46,2823-2825
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |