Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts

被引：131

作者：

Santhoshkumar, Rajagopal ^{[1
]}

Mannathan, Subramaniyan ^{[1
]}

Cheng, Chien-Hong ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 51期

关键词：

S-SUBSTITUTED ALDEHYDES; INTERMOLECULAR HYDROACYLATION; INTRAMOLECULAR HYDROACYLATION; BOND ACTIVATION; COUPLING REACTION; OXIDATION LEVEL; ALKYL ALDEHYDES; BORONIC ACIDS; ARYL KETONES; ATOM ECONOMY;

D O I：

10.1021/jacs.5b10447

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a highly step and atom economical cobalt-catalyzed cydization of 1,6-enynes with aldehydes to synthesize functionalized pyrrolidines and dihydrofurans with high chemo- and stereoselectivity. The catalytic reaction plausibly proceeds via the cobaltacycle intermediate generated from the reaction of enyne substrate with cobalt catalyst, followed by switchable C-H functionalization of weakly coordinating aldehydes depending on the electronic nature of the ligand.

引用

收藏

页码：16116 / 16120

页数：5

相关论文

共 97 条

[71] Nickel-catalyzed cycloadditions of unsaturated hydrocarbons, aldehydes, and ketones [J].

Tekavec, Thomas N. ;

Louie, Janis .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2641-2648

[72] Multiple arylation of alkyl aryl ketones and α,β-unsaturated carbonyl compounds via palladium catalysis [J].

Terao, Y ;

Kametani, Y ;

Wakui, H ;

Satoh, T ;

Miura, M ;

Nomura, M .

TETRAHEDRON, 2001, 57 (28) :5967-5974

[73] THE ATOM ECONOMY - A SEARCH FOR SYNTHETIC EFFICIENCY [J].

TROST, BM .

SCIENCE, 1991, 254 (5037) :1471-1477

[74] On inventing reactions for atom economy [J].

Trost, BM .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :695-705

[75] ATOM ECONOMY - A CHALLENGE FOR ORGANIC-SYNTHESIS - HOMOGENEOUS CATALYSIS LEADS THE WAY [J].

TROST, BM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (03) :259-281

[76]

Trost BM, 1998, SYNLETT, P1

[77] NICKEL(0)-CATALYZED HYDROACYLATION OF ALKYNES WITH ALDEHYDES TO ALPHA,BETA-ENONES [J].

TSUDA, T ;

KIYOI, T ;

SAEGUSA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2554-2558

[78] From Highly Enantioselective Catalytic Reaction of 1,3-Diynes with Aldehydes to Facile Asymmetric Synthesis of Polycyclic Compounds [J].

Turlington, Mark ;

Du, Yuhao ;

Ostrum, Samuel G. ;

Santosh, Vishaka ;

Wren, Kathryne ;

Lin, Tony ;

Sabat, Michal ;

Pu, Lin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (30) :11780-11794

[79] Cobalt-catalyzed highly regio- and stereoselective intermolecular reductive coupling of alkynes with conjugated alkenes [J].

Wang, CC ;

Lin, PS ;

Cheng, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9696-9697

[80] Rhodium-Catalyzed Cyclization of Diynes with Nitrones: A Formal [2+2+5] Approach to Bridged Eight-Membered Heterocycles [J].

Wang, Chunxiang ;

Wang, Dongping ;

Yan, Hao ;

Wang, Haolong ;

Pan, Bin ;

Xin, Xiaoyi ;

Li, Xincheng ;

Wu, Fan ;

Wan, Boshun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) :11940-11943

← 1 2 3 4 5 6 7 8 9 10 →