基于经济绿色催化体系的新型碳—碳成键反应研究
摘要
利用直接芳基化(芳基C-H键活化)反应策略,首次实现了利用经济绿色铁催化剂催化的非活化芳烃与各种芳基卤代物的直接芳基化反应合成联芳烃化合物。该反应催化体系简单,利用FeCl3作为催化剂,N,N’-二甲基乙二胺(DMEDA)作为配体,六甲基二硅胺基锂(LiHMDS)作碱。反应底物适用范围较广,芳基卤代物包括了芳基碘代物、芳基溴代物及低反应活性的芳基氯代物；参与反应的非活化芳烃包括了苯、甲苯、苯甲醚、萘、以及二茂铁。同时发现该反应通过了自由基反应历程。
研究并发现了在催化量(20%)的有机小分子(DMEDA等)存在条件下,反应加入当量的叔丁醇钾,各种芳基碘代物能与苯等非活化芳烃进行直接芳基化反应实现联芳烃化合物的合成。研究并且发现该直接芳基化反应通过了自由基反应历程实现。
利用直接芳基化反应策略,首次实现了廉价钴盐催化的非活化芳烃(苯,甲苯,萘等)与芳基卤代物的直接芳基化反应高产率地合成联芳烃类化合物。反应底物适用范围广,芳基卤代物包括芳基碘代物、芳基溴代物及反应活性较低的芳基氯代物。同时该反应还能较好地实现分子内的直接芳基化反应。
本文采用氧化偶联反应策略,利用廉价绿色氧气作为氧化剂,研究并实现了在室温条件下的廉价绿色铁催化的芳基格氏试剂的高效氧化自偶联反应合成联芳烃化合物。同时发现该反应在直接利用空气作为氧化剂的条件下也能较好地进行。
利用氧化偶联反应策略,直接用氧气作为氧化剂,一氧化碳气体作为羰基源,研究并实现了钴催化的芳基锌试剂的氧化羰基化反应高效地合成对称的二芳基甲酮类化合物。该反应选择性好,不需外加配体,在室温常压下即可进行。
The aromatic C-H functionalization or direct arylation of aromatic C-H is one of the hottest research areas in the construction of biaryl motifs. The successful catalysts reported have focused on Pd, Ir, Rh, Ru, Cu and Ni etc. Herein, we first reported the iron-catalyzed direct arylation of unactivated arenes with aryl halides. At a relatively mild temperature, using DMEDA as ligand and LiHMDS as base, the aromatic C-H functionalization with various aryl halides including aryl iodides, aryl bromides and chlorides was achieved by cheap iron catalyst. The unactivated arenes include benzene, toluene, anisole and ferrocene. Moreover, aryl radical pathway was involved in the direct arylation.
We first developed the organomolecule-catalyzed direct arylation of unactivated benzene with various aryl iodides to produce biaryls. The catalytical amount of DMEDA was essential for the success of the direct arylation of benzene in the presence of potassium tert-butoxide at 80℃. And further investigation on the reaction mechanism indicated that aryl radical was involved in this transformation.
Furthermore, cobalt-catalyzed direct arylation of unactivated arenes with aryl halides was explored. Excellent yields were achieved using solely cobalt salt without adding extra ligands especially for aryl bromides and aryl iodides in the presence of LiHMDS base. And intramolecular direct arylation was achieved under the same reaction conditions.
Oxidative coupling is one of most important coupling approaches to construct C-C bonds. The oxidants used in transition-metal-catalyzed oxidative coupling reactions were mainly focused on organic oxidants and inorganic oxidants, which would produce wastes and bring difficulties to isolation and purification. We employed green and cheap oxidant oxygen in the iron-catalyzed oxidative homo-coupling of aryl Grignard reagents to the facile synthesis of biaryls. The benefits of the above method are green oxidant O2, cheap and non-toxic iron catalyst and mild reaction conditions.
Using the oxidative coupling methods, we explored the cobalt-catalyzed oxidative carbonylation of various aryl zinc reagents using oxygen as the oxidant to the facile synthesis of aryl ketones. High yields and excellent selectivity were achieved under very mild conditions without adding extra ligands.
研究并发现了在催化量(20%)的有机小分子(DMEDA等)存在条件下,反应加入当量的叔丁醇钾,各种芳基碘代物能与苯等非活化芳烃进行直接芳基化反应实现联芳烃化合物的合成。研究并且发现该直接芳基化反应通过了自由基反应历程实现。
利用直接芳基化反应策略,首次实现了廉价钴盐催化的非活化芳烃(苯,甲苯,萘等)与芳基卤代物的直接芳基化反应高产率地合成联芳烃类化合物。反应底物适用范围广,芳基卤代物包括芳基碘代物、芳基溴代物及反应活性较低的芳基氯代物。同时该反应还能较好地实现分子内的直接芳基化反应。
本文采用氧化偶联反应策略,利用廉价绿色氧气作为氧化剂,研究并实现了在室温条件下的廉价绿色铁催化的芳基格氏试剂的高效氧化自偶联反应合成联芳烃化合物。同时发现该反应在直接利用空气作为氧化剂的条件下也能较好地进行。
利用氧化偶联反应策略,直接用氧气作为氧化剂,一氧化碳气体作为羰基源,研究并实现了钴催化的芳基锌试剂的氧化羰基化反应高效地合成对称的二芳基甲酮类化合物。该反应选择性好,不需外加配体,在室温常压下即可进行。
The aromatic C-H functionalization or direct arylation of aromatic C-H is one of the hottest research areas in the construction of biaryl motifs. The successful catalysts reported have focused on Pd, Ir, Rh, Ru, Cu and Ni etc. Herein, we first reported the iron-catalyzed direct arylation of unactivated arenes with aryl halides. At a relatively mild temperature, using DMEDA as ligand and LiHMDS as base, the aromatic C-H functionalization with various aryl halides including aryl iodides, aryl bromides and chlorides was achieved by cheap iron catalyst. The unactivated arenes include benzene, toluene, anisole and ferrocene. Moreover, aryl radical pathway was involved in the direct arylation.
We first developed the organomolecule-catalyzed direct arylation of unactivated benzene with various aryl iodides to produce biaryls. The catalytical amount of DMEDA was essential for the success of the direct arylation of benzene in the presence of potassium tert-butoxide at 80℃. And further investigation on the reaction mechanism indicated that aryl radical was involved in this transformation.
Furthermore, cobalt-catalyzed direct arylation of unactivated arenes with aryl halides was explored. Excellent yields were achieved using solely cobalt salt without adding extra ligands especially for aryl bromides and aryl iodides in the presence of LiHMDS base. And intramolecular direct arylation was achieved under the same reaction conditions.
Oxidative coupling is one of most important coupling approaches to construct C-C bonds. The oxidants used in transition-metal-catalyzed oxidative coupling reactions were mainly focused on organic oxidants and inorganic oxidants, which would produce wastes and bring difficulties to isolation and purification. We employed green and cheap oxidant oxygen in the iron-catalyzed oxidative homo-coupling of aryl Grignard reagents to the facile synthesis of biaryls. The benefits of the above method are green oxidant O2, cheap and non-toxic iron catalyst and mild reaction conditions.
Using the oxidative coupling methods, we explored the cobalt-catalyzed oxidative carbonylation of various aryl zinc reagents using oxygen as the oxidant to the facile synthesis of aryl ketones. High yields and excellent selectivity were achieved under very mild conditions without adding extra ligands.
引文
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