Palladium-Catalyzed Minisci Reaction with Simple Alcohols

被引:113
作者
Correia, Camille A. [1 ]
Yang, Luo [1 ]
Li, Chao-Jun [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
CROSS-COUPLING REACTION; FREE-RADICAL REACTIONS; C-H ACTIVATION; TRANSFER HYDROGENATION; BOND FORMATION; ALKYNES;
D O I
10.1021/ol201774b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed coupling of N-heterocycles with simple alcohols was achieved. The reaction is initiated by peroxide and does not require the use of stoichlometric acid for activation of the heterocycle.
引用
收藏
页码:4581 / 4583
页数:3
相关论文
共 20 条
[1]   Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents [J].
Bower, John F. ;
Kim, In Su ;
Patman, Ryan L. ;
Krische, Michael J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :34-46
[2]  
Castellano A., 1974, CHEM HETEROCYCL COMP, V10, P755
[3]   ALPHA-HYDROXYALKYLATION OF HETEROAROMATIC BASES BY ALCOHOLS AND HYDROXYLAMINE-O-SULFONIC ACID [J].
CITTERIO, A ;
GENTILE, A ;
MINISCI, F ;
SERRAVALLE, M ;
VENTURA, S .
TETRAHEDRON, 1985, 41 (03) :617-620
[4]   Coupling of Nitrogen Heteroaromatics and Alkanes without Transition Metals: A New Oxidative Cross-Coupling at C-H/C-H Bonds [J].
Deng, Guojun ;
Ueda, Kirika ;
Yanagisawa, Shuichi ;
Itami, Kenichiro ;
Li, Chao-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (02) :333-337
[5]   Sc(OTf)3-Catalyzed Direct Alkylation of Quinolines and Pyridines with Alkanes [J].
Deng, Guojun ;
Li, Chao-Jun .
ORGANIC LETTERS, 2009, 11 (05) :1171-1174
[6]   Palladium-catalyzed/Lewis acid-promoted alkene dimerization and cross-coupling with alcohols via C-H bond activation [J].
Jiang, Yi-Jun ;
Tu, Yong-Qiang ;
Zhang, En ;
Zhang, Shu-Yu ;
Cao, Ke ;
Shi, Lei .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (04) :552-556
[7]   Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].
Li, Chao-Jun .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344
[8]   Free-Radical-Initiated Coupling Reaction of Alcohols and Alkynes: Not C-O but C-C Bond Formation [J].
Liu, Zhong-Quan ;
Sun, Liang ;
Wang, Jian-Guo ;
Han, Jie ;
Zhao, Yan-Kai ;
Zhou, Bo .
ORGANIC LETTERS, 2009, 11 (06) :1437-1439
[9]   POLAR EFFECTS IN FREE-RADICAL REACTIONS - SELECTIVITY AND REVERSIBILITY IN THE HOMOLYTIC BENZYLATION OF PROTONATED HETEROAROMATIC BASES [J].
MINISCI, F ;
VISMARA, E ;
MORINI, G ;
FONTANA, F ;
LEVI, S ;
SERRAVALLE, M ;
GIORDANO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :476-479
[10]   NOVEL APPLICATIONS OF FREE-RADICAL REACTIONS IN PREPARATIVE ORGANIC-CHEMISTRY [J].
MINISCI, F .
SYNTHESIS-STUTTGART, 1973, (01) :1-24