过渡金属催化炔烃环化反应的研究进展
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摘要
具有独特反应性和稳定性的炔烃类化合物一直以来是科研工作者们关注的热点之一,其中关于炔烃环化构筑一系列多环化合物的反应报道尤为突出。本文根据不同金属催化剂,总结归纳了近几年铑、钌、钴、钯等过渡金属催化炔烃环化反应的研究进展,并简要讨论了催化转化的反应机理、优势以及局限性,最后展望了过渡金属催化炔烃环化反应的发展前景。
With the especial reactivity and stability,the alkynes had been one of the research hotspots for constructing a series of polycyclic compounds.In this review,the up-to-date summaries of transition-metal-catalyzed cyclization of alkynes on the basis of metal catalysts such as rhodium,ruthenium,cobalt and palladium were gave.It was pointed out that the plausible mechanisms,advantages and limitations in these transformations.Finally,the outlooks for transition-metal-catalyzed cyclization of alkynes was suggested.
With the especial reactivity and stability,the alkynes had been one of the research hotspots for constructing a series of polycyclic compounds.In this review,the up-to-date summaries of transition-metal-catalyzed cyclization of alkynes on the basis of metal catalysts such as rhodium,ruthenium,cobalt and palladium were gave.It was pointed out that the plausible mechanisms,advantages and limitations in these transformations.Finally,the outlooks for transition-metal-catalyzed cyclization of alkynes was suggested.
引文
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[9]Li X,Pan J,Wu H,et al.Rh-catalyzed aerobic oxidative cyclization of anilines,alkynes,and CO[J].Chem Sci,2017,8(9):6 266-6 273.
[10]Manan R,Zhao P.Merging rhodium-catalysed C-H activation and hydroamination in a highly selective[4+2]imine/alkyne annulation[J].Nat Commun,2016,7:11 506-11 516.
[11]Zhou M,Pi R,Hu M,et al.Rhodium(III)-Catalyzed[3+2]annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp2)-H/alkene functionalization[J].Angew Chem Int Ed,2014,53(42):11 338-11 341.
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[13]Zheng J,Wang S,Zheng C,et al.Asymmetric synthesis of spiropyrazolones by rhodium-catalyzed C(sp2)-H functionalization/annulation reactions[J].Angew Chem Int Ed,2017,56(16):4 540-4 544.
[14]Liu X,Li G,Song F,et al.Unexpected regioselective carbon-hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles[J].Nat Commun,2014,5:5 030-5 037.
[15]Liu X,Li X,Liu H,et al.Aldehyde as a traceless directing group for Rh(III)-catalyzed C-H activation:a facile access to diverse indolo[1,2-a]quinolones[J].Org Lett,2015,17(12):2 936-2 939.
[16]Zhao Y,Li S,Zheng X,et al.Rh/Cu-catalyzed cascade[4+2]vinylic C-H O-annulation and ring contraction of α-aryl enones with alkynes in air[J].Angew Chem Int Ed,2017,56(15):4 286-4 289.
[17]Yin J,Tan M,Wu D,et al.Synthesis of diverse phenalenyl-fused pyrylium cations via divergent cascade C-H activation/annulations of naphthalene aldehydes with alkynes[J].Angew Chem Int Ed,2017,56(42):13 094-13 098.
[18]Ackermann,L.Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C-H/Het-H bond functionalizations[J].Acc Chem Res,2014,47(2):281-295.
[19]Warratz S,Kornhaaв C,Cajaraville A,et al.Ruthenium(II)-catalyzed C-H activation/alkyne annulation by weak coordination with O2 as the sole oxidant[J].Angew Chem Int Ed,2015,54(18):5 513-5 517.
[20]Qiu Y,Tian C,Massignan L,et al.Electrooxidative ruthenium-catalyzed C-H/O-H annulation by weak O-coordination[J].Angew Chem Int Ed,2018,57(20):5 818-5 822.
[21]Chinchilla R,Najera C.Chemicals from alkynes with palladium catalysts[J].Chem Rev,2014,114(3):1 783-1 826.
[22]Ling F,Li Z,Zheng C,et al.Palladium/Copper-catalyzed aerobic intermolecular cyclization of enediyne compounds and alkynes:interrupting cycloaromatization for(4+2)cross-benzannulation[J].J Am Chem Soc,2014,136(31),10 914-10 917.
[23]Zuo Z,Liu J,Nan J,et al.Highly stereoselective synthesis of imine-containing dibenzo[b,d]azepines by a palladium(II)-catalyzed[5+2]oxidative annulation of o-arylanilines with alkynes[J].Angew Chem Int Ed,2015,54(51):15 385-15 389.
[24]Zhao Q,Fu W,Kwong F.Palladium-catalyzed regioselective aromatic extension of internal alkynes through a norbornene-controlled reaction sequence[J].Angew Chem Int Ed,2018,57(13):3 381-3 385.
[25]Prakash S,Kuppusamy R,Cheng C,et al.Cobalt-catalyzed annulation reactions via C-H bond activation[J].Chem Cat Chem,2018,10(4):683-705.
[26]Tian C,Massignan L,Meyer T,et al.Electrochemical C-H/N-H activation by water-tolerant cobalt catalysis at room temperature[J].Angew Chem Int Ed,2018,57(9):2 383-2 387.
[27]Mei R,Sauermann N,Oliveira J,et al.Electroremovable traceless hydrazides for cobalt-catalyzed electro-oxidative C-H/N-H activation with internal alkynes[J].J Am Chem Soc,2018,140(25):7 913-7 921.
[28]Tang S,Wang D,Liu Y,et al.Cobalt-catalyzed electrooxidative C-H/N-H[4+2]annulation with ethylene or ethyne[J].Nat Commun,2018,9:798-804.
[29]Zhang G,Lin Y,Luo X,et al.Oxidative[4+2]annulation of styrenes with alkynes under external-oxidant-free conditions[J].Nat Commun,2018,9:1 225-1 231.
[30]Tian W,Wang D,Wang S,et al.Visible-Light photoredox-catalyzed iminyl radical formation by N-H cleavage with hydrogen release and its application in synthesis of isoquinolines[J].Org Lett,2018,20(5):1 421-1 425.
[31]Ikemoto H,Yoshino T,Sakata K,et al.Pyrroloindolone synthesis via a Cp*CoIII-catalyzed redox-neutral directed C-H alkenylation/annulation sequence[J].J Am Chem Soc,2014,136(14):5 424-5 431.
[32]Sun B,Yoshino T,Kanai M,et al.Cp*CoIII catalyzed site-selective C-H activation of unsymmetrical O-acyl oximes:synthesis of multisubstituted isoquinolines from terminal and internal alkynes[J].Angew Chem Int Ed,2015,54(44):12 968-12 972.
[33]Prakash S,Muralirajan K,Cheng C.Cobalt-catalyzed oxidative annulation of nitrogen-containing arenes with alkynes:an atom-economical route to heterocyclic quaternary ammonium salts[J].Angew Chem Int Ed,2016,55(5):1 844-1 848.
[34]Sanjos-Orduna J,Gallego D,Garcia-Roca A,et al.Capturing elusive cobaltacycle intermediates:a real-time snapshot of the Cp*CoIII-catalyzed oxidative alkyne annulation[J].Angew Chem Int Ed,2017,56(40):12 137-12 141.
[35]Lerchen A,Vasquez-Cespedes S,Glorius F.Cobalt(III)-catalyzed redox-neutral synthesis of unprotecte indoles featuring an N-N bond cleavage[J].Angew Chem Int Ed,2016,55(9):3 208-3 211.
[36]Liang Y,Jiao N.Cationic cobalt(III)catalyzed indole synthesis:the regioselective intermolecular cyclization of N-nitrosoanilines and alkynes[J].Angew Chem Int Ed,2016,55(12):4 035-4 039.
[37]Sagadevan A,Ragupathi A,Hwang K.Photoinduced copper-catalyzed regioselective synthesis of indoles:three-component coupling of arylamines,terminal alkynes,and quinones[J].Angew Chem Int Ed,2015,54(47):13 896-13 901.
[38]Liang Y,Steinbock R,Münch A,et al.Manganese-catalyzed carbonylative annulations for redox-neutral late-stage diversification[J].Angew Chem Int Ed,2018,57(19):5 384-5 388.
[39]He R,Huang Z,Zheng Q,et al.Manganese-catalyzed dehydrogenative[4+2]annulation of N-H imines and alkynes by C-H/N-H activation[J].Angew Chem Int Ed,2014,53(19):4 950-4 953.
[40]Lu Q,Greвies S,Cembellin S,et al.Redox-neutral manganese(I)-catalyzed C-H activation:traceless directing group enabled regioselective annulation[J].Angew Chem Int Ed,2017,56(41):12 778-12 782.
[41]Jia T,Zhao C,He R,et al.Iron-carbonyl-catalyzed redox-neutral[4+2]annulation of N-H imines and internal alkynes by C-H bond activation[J].Angew Chem Int Ed,2016,55(17):5 268-5 271.
[42]Hung C,Gandeepan P,Cheng L,et al.Experimental and theoretical studies on iron-promoted oxidative annulation of arylglyoxal with alkyne:unusual addition and migration on the aryl ring[J].J Am Chem Soc,2017,139(47):17 015-17 021.
[2]Lei J,Su L,Zeng K,et al.Recent advances of catalytic processes on the transformation of alkynes into functional compounds[J].Chem Eng Sci,2017,171:404-425.
[3]Gulias M,Mascarenas J.Metal-catalyzed annulations through activation and cleavage of C-H bonds[J].Angew Chem Int Ed,2016,55(37):11 000-11 019.
[4]Minami Y,Hiyama T.Recent topics in annulation reaction via double C-H bond cleavage and double C-C bond formation[J].Tetrahedron Lett,2018,59:781-788.
[5]Song G,Wang F,Li X.C-C,C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation[J].Chem Soc Rev,2012,41(9):3 651-3 678.
[6]Yang Y,Li K,Cheng Y,et al.Rhodium-catalyzed annulation of arenes with alkynes through weakly chelation-assisted C-H activation[J].Chem Commun,2016,52(14):2 872-2 884.
[7]Dutta C,Choudhury J.C-H activation-annulation on the N-heterocyclic carbene platform[J].RSC Adv,2018,8(49):27 881-27 891.
[8]Li X,Li X,Jiao N.Rh-Catalyzed quinolin-2(1H)-one construction via C-H bond activation of simple anilines with CO and alkynes[J].J Am Chem Soc,2015,137(29):9 246-9 249.
[9]Li X,Pan J,Wu H,et al.Rh-catalyzed aerobic oxidative cyclization of anilines,alkynes,and CO[J].Chem Sci,2017,8(9):6 266-6 273.
[10]Manan R,Zhao P.Merging rhodium-catalysed C-H activation and hydroamination in a highly selective[4+2]imine/alkyne annulation[J].Nat Commun,2016,7:11 506-11 516.
[11]Zhou M,Pi R,Hu M,et al.Rhodium(III)-Catalyzed[3+2]annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp2)-H/alkene functionalization[J].Angew Chem Int Ed,2014,53(42):11 338-11 341.
[12]Yang Y,Zhou M,Ouyang X,et al.Rhodium(III)-Catalyzed[3+2]/[5+2]annulation of 4-aryl 1,2,3-triazoles with internal alkynes through dual C(sp2)-H functionalization[J].Angew Chem Int Ed,2015,54(22):6 595-6 599.
[13]Zheng J,Wang S,Zheng C,et al.Asymmetric synthesis of spiropyrazolones by rhodium-catalyzed C(sp2)-H functionalization/annulation reactions[J].Angew Chem Int Ed,2017,56(16):4 540-4 544.
[14]Liu X,Li G,Song F,et al.Unexpected regioselective carbon-hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles[J].Nat Commun,2014,5:5 030-5 037.
[15]Liu X,Li X,Liu H,et al.Aldehyde as a traceless directing group for Rh(III)-catalyzed C-H activation:a facile access to diverse indolo[1,2-a]quinolones[J].Org Lett,2015,17(12):2 936-2 939.
[16]Zhao Y,Li S,Zheng X,et al.Rh/Cu-catalyzed cascade[4+2]vinylic C-H O-annulation and ring contraction of α-aryl enones with alkynes in air[J].Angew Chem Int Ed,2017,56(15):4 286-4 289.
[17]Yin J,Tan M,Wu D,et al.Synthesis of diverse phenalenyl-fused pyrylium cations via divergent cascade C-H activation/annulations of naphthalene aldehydes with alkynes[J].Angew Chem Int Ed,2017,56(42):13 094-13 098.
[18]Ackermann,L.Carboxylate-assisted ruthenium-catalyzed alkyne annulations by C-H/Het-H bond functionalizations[J].Acc Chem Res,2014,47(2):281-295.
[19]Warratz S,Kornhaaв C,Cajaraville A,et al.Ruthenium(II)-catalyzed C-H activation/alkyne annulation by weak coordination with O2 as the sole oxidant[J].Angew Chem Int Ed,2015,54(18):5 513-5 517.
[20]Qiu Y,Tian C,Massignan L,et al.Electrooxidative ruthenium-catalyzed C-H/O-H annulation by weak O-coordination[J].Angew Chem Int Ed,2018,57(20):5 818-5 822.
[21]Chinchilla R,Najera C.Chemicals from alkynes with palladium catalysts[J].Chem Rev,2014,114(3):1 783-1 826.
[22]Ling F,Li Z,Zheng C,et al.Palladium/Copper-catalyzed aerobic intermolecular cyclization of enediyne compounds and alkynes:interrupting cycloaromatization for(4+2)cross-benzannulation[J].J Am Chem Soc,2014,136(31),10 914-10 917.
[23]Zuo Z,Liu J,Nan J,et al.Highly stereoselective synthesis of imine-containing dibenzo[b,d]azepines by a palladium(II)-catalyzed[5+2]oxidative annulation of o-arylanilines with alkynes[J].Angew Chem Int Ed,2015,54(51):15 385-15 389.
[24]Zhao Q,Fu W,Kwong F.Palladium-catalyzed regioselective aromatic extension of internal alkynes through a norbornene-controlled reaction sequence[J].Angew Chem Int Ed,2018,57(13):3 381-3 385.
[25]Prakash S,Kuppusamy R,Cheng C,et al.Cobalt-catalyzed annulation reactions via C-H bond activation[J].Chem Cat Chem,2018,10(4):683-705.
[26]Tian C,Massignan L,Meyer T,et al.Electrochemical C-H/N-H activation by water-tolerant cobalt catalysis at room temperature[J].Angew Chem Int Ed,2018,57(9):2 383-2 387.
[27]Mei R,Sauermann N,Oliveira J,et al.Electroremovable traceless hydrazides for cobalt-catalyzed electro-oxidative C-H/N-H activation with internal alkynes[J].J Am Chem Soc,2018,140(25):7 913-7 921.
[28]Tang S,Wang D,Liu Y,et al.Cobalt-catalyzed electrooxidative C-H/N-H[4+2]annulation with ethylene or ethyne[J].Nat Commun,2018,9:798-804.
[29]Zhang G,Lin Y,Luo X,et al.Oxidative[4+2]annulation of styrenes with alkynes under external-oxidant-free conditions[J].Nat Commun,2018,9:1 225-1 231.
[30]Tian W,Wang D,Wang S,et al.Visible-Light photoredox-catalyzed iminyl radical formation by N-H cleavage with hydrogen release and its application in synthesis of isoquinolines[J].Org Lett,2018,20(5):1 421-1 425.
[31]Ikemoto H,Yoshino T,Sakata K,et al.Pyrroloindolone synthesis via a Cp*CoIII-catalyzed redox-neutral directed C-H alkenylation/annulation sequence[J].J Am Chem Soc,2014,136(14):5 424-5 431.
[32]Sun B,Yoshino T,Kanai M,et al.Cp*CoIII catalyzed site-selective C-H activation of unsymmetrical O-acyl oximes:synthesis of multisubstituted isoquinolines from terminal and internal alkynes[J].Angew Chem Int Ed,2015,54(44):12 968-12 972.
[33]Prakash S,Muralirajan K,Cheng C.Cobalt-catalyzed oxidative annulation of nitrogen-containing arenes with alkynes:an atom-economical route to heterocyclic quaternary ammonium salts[J].Angew Chem Int Ed,2016,55(5):1 844-1 848.
[34]Sanjos-Orduna J,Gallego D,Garcia-Roca A,et al.Capturing elusive cobaltacycle intermediates:a real-time snapshot of the Cp*CoIII-catalyzed oxidative alkyne annulation[J].Angew Chem Int Ed,2017,56(40):12 137-12 141.
[35]Lerchen A,Vasquez-Cespedes S,Glorius F.Cobalt(III)-catalyzed redox-neutral synthesis of unprotecte indoles featuring an N-N bond cleavage[J].Angew Chem Int Ed,2016,55(9):3 208-3 211.
[36]Liang Y,Jiao N.Cationic cobalt(III)catalyzed indole synthesis:the regioselective intermolecular cyclization of N-nitrosoanilines and alkynes[J].Angew Chem Int Ed,2016,55(12):4 035-4 039.
[37]Sagadevan A,Ragupathi A,Hwang K.Photoinduced copper-catalyzed regioselective synthesis of indoles:three-component coupling of arylamines,terminal alkynes,and quinones[J].Angew Chem Int Ed,2015,54(47):13 896-13 901.
[38]Liang Y,Steinbock R,Münch A,et al.Manganese-catalyzed carbonylative annulations for redox-neutral late-stage diversification[J].Angew Chem Int Ed,2018,57(19):5 384-5 388.
[39]He R,Huang Z,Zheng Q,et al.Manganese-catalyzed dehydrogenative[4+2]annulation of N-H imines and alkynes by C-H/N-H activation[J].Angew Chem Int Ed,2014,53(19):4 950-4 953.
[40]Lu Q,Greвies S,Cembellin S,et al.Redox-neutral manganese(I)-catalyzed C-H activation:traceless directing group enabled regioselective annulation[J].Angew Chem Int Ed,2017,56(41):12 778-12 782.
[41]Jia T,Zhao C,He R,et al.Iron-carbonyl-catalyzed redox-neutral[4+2]annulation of N-H imines and internal alkynes by C-H bond activation[J].Angew Chem Int Ed,2016,55(17):5 268-5 271.
[42]Hung C,Gandeepan P,Cheng L,et al.Experimental and theoretical studies on iron-promoted oxidative annulation of arylglyoxal with alkyne:unusual addition and migration on the aryl ring[J].J Am Chem Soc,2017,139(47):17 015-17 021.