Efficient Rh(I)-Catalyzed Direct Arylation and Alkenylation of Arene C-H Bonds via Decarbonylation of Benzoic and Cinnamic Anhydrides

被引:95
作者
Jin, Weiwei [1 ,2 ]
Yu, Zhengkun [1 ]
He, Wei [1 ]
Ye, Wenjing [1 ]
Xiao, Wen-Jing [2 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China
[2] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED DIRECT ARYLATION; PYRIDINE-N-OXIDES; UNACTIVATED ARENES; CARBOXYLIC-ACIDS; DIETHYL AZODICARBOXYLATE; DIRECT FUNCTIONALIZATION; SELECTIVE ALKENYLATION; COUPLING REACTION; TERMINAL ALKYNES; BORONIC ACIDS;
D O I
10.1021/ol9000729
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient rhodium(I)-catalyzed regioselective direct arylation and alkenylation of aromatic C-H bonds has been realized with aromatic carboxylic and cinnamic anhydrides as the coupling partners via decarbonylation and C-H activation under phosphine-free conditions.
引用
收藏
页码:1317 / 1320
页数:4
相关论文
共 67 条
[41]   The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates [J].
Matsuura, Yusuke ;
Tamura, Masaru ;
Kochi, Takuya ;
Sato, Mitsuo ;
Chatani, Naoto ;
Kakiuchi, Fumitoshi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) :9858-+
[42]   A strategy for C-H activation of pyridines: Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis [J].
Nakao, Yoshiaki ;
Kanyiva, Kyalo Stephen ;
Hiyama, Tamejiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2448-2449
[43]   Iron-catalyzed direct arylation through directed C-H bond activation [J].
Norinder, Jakob ;
Matsumoto, Arimasa ;
Yoshikai, Naohiko ;
Nakamura, Eiichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (18) :5858-+
[44]   PALLADIUM-CATALYZED DECARBONYLATIVE COUPLING OF ACID-CHLORIDES, ORGANODISILANES, AND 1,3-DIENES [J].
OBORA, Y ;
TSUJI, Y ;
KAWAMURA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10414-10415
[45]   Rhodium-catalysed direct ortho arylation of 2-arylpyridines with arylstannanes via C-H activation [J].
Oi, S ;
Fukita, S ;
Inoue, Y .
CHEMICAL COMMUNICATIONS, 1998, (22) :2439-2440
[46]   Direct arylation of arene C-H bonds by cooperative action of NHCarbene-Ruthenium(II) catalyst and carbonate via proton abstraction mechanism [J].
Ozdemir, Ismail ;
Demir, Serpil ;
Cetinkaya, Bekir ;
Gourlaouen, Christophe ;
Maseras, Feliu ;
Bruneau, Christian ;
Dixneuf, Pierre H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) :1156-+
[47]   PdII-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands [J].
Shi, Bing-Feng ;
Maugel, Nathan ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4882-4886
[48]   Suzuki-Miyaura coupling reaction by PdII-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group [J].
Shi, Zhangjie ;
Li, Bijie ;
Wan, Xiaobing ;
Cheng, Jiang ;
Fang, Zhao ;
Cao, Bin ;
Qin, Changming ;
Wang, Yang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5554-5558
[49]   An Au-catalyzed cyclialkylation of electron-rich arenes with epoxides to prepare 3-chromanols [J].
Shi, ZJ ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5964-5965
[50]   Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III) [J].
Shi, ZJ ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13596-13597