Copper- and Cobalt-Catalyzed Direct Coupling of sp3 α-Carbon of Alcohols with Alkenes and Hydroperoxides

被引：186
作者：
Cheng, Jun-Kee [2 ]
Loh, Teck-Peng [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 01期
关键词：
C-H FUNCTIONALIZATION; CARBONYLATION-PEROXIDATION; ASYMMETRIC ADDITION; GRIGNARD-REAGENTS; BOND FUNCTIONALIZATION; NUCLEOPHILIC-ADDITION; C(SP(3))-H BONDS; ETHERS; ALDEHYDES; ACTIVATION;
D O I：
10.1021/ja510635k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A zerovalent copper- and cobalt-catalyzed direct coupling of the sp(3) alpha-carbon of alcohols with alkenes and hydroperoxides was developed in which the hydroperoxides acted as radical initiator and then coupling partner. 1,3-Enynes and vinylarenes underwent alkylation-peroxidation to give beta-peroxy alcohols and beta-hydroxyketones correspondingly with excellent functional group tolerance. The resulting beta-peroxy alcohols could be further transformed into beta-hydroxyynones and propargylic 1,3-diols.
引用
收藏
页码：42 / 45
页数：4
相关论文
共 87 条
[1]  
Abdel-Magid A. F., 2014, Comprehensive Organic Synthesis, V8, P1, DOI DOI 10.1016/B978-0-08-097742-3.00801-6
[2]  
Blinder C. M., 2009, J ORG CHEM, V74, P2337
[3]   Regioselective Ruthenium Catalyzed Hydrohydroxyalkylation of Dienes with 3-Hydroxy-2-oxindoles: Prenylation, Geranylation, and Beyond [J].
Chen, Te-Yu ;
Krische, Michael J. .
ORGANIC LETTERS, 2013, 15 (12) :2994-2997
[4]   ABSOLUTE RATE CONSTANTS FOR HYDROCARBON AUTOXIDATION .25. RATE CONSTANTS FOR HYDROGEN-ATOM ABSTRACTION FROM ALKANES BY THE TERT-BUTYLPEROXY RADICAL [J].
CHENIER, JHB ;
TONG, SB ;
HOWARD, JA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (24) :3047-3053
[5]   Metal-free oxidative direct C(sp3)-H bond functionalization of ethers with α,α-diaryl allylic alcohols [J].
Chu, Xue-Qiang ;
Meng, Hua ;
Zi, You ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMICAL COMMUNICATIONS, 2014, 50 (68) :9718-9721
[6]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[7]  
2-Z
[8]   Palladium-Catalyzed Minisci Reaction with Simple Alcohols [J].
Correia, Camille A. ;
Yang, Luo ;
Li, Chao-Jun .
ORGANIC LETTERS, 2011, 13 (17) :4581-4583
[9]   Copper-catalyzed decarboxylative alkenylation of sp3 C-H bonds with cinnamic acids via a radical process [J].
Cui, Zili ;
Shang, Xiaojie ;
Shao, Xiang-Feng ;
Liu, Zhong-Quan .
CHEMICAL SCIENCE, 2012, 3 (09) :2853-2858
[10]   Magnesium/methanol: Sn effective reducing agent for peroxides [J].
Dai, P ;
Dussault, PH ;
Trullinger, TK .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2851-2852
123456789