Cu-catalyzed cross-dehydrogenative coupling:: A versatile strateav for C-C bond formations via the oxidative activation of sp3 C-H bonds

被引：564

作者：

Li, Zhiping ^{[1
]}

Bohle, D. Scott ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA | 2006年 / 103卷 / 24期

关键词：

C-H activation; catalysis; Baylis-Hillman reaction; Mannich reaction; Friedel-crafts reaction;

D O I：

10.1073/pnas.0601687103

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Cu-catalyzed cross-dehydrogenative coupling (CDC) methodologies were developed based on the oxidative activation of sp(3) C-H bonds adjacent to a nitrogen atom. Various sp, sp(2), and sp(3) C-H bonds of pronucleophiles were used in the Cu-catalyzed CDC reactions. Based on these results, the mechanisms of the CDC reactions also are discussed.

引用

收藏

页码：8928 / 8933

页数：6

相关论文

共 90 条

[1] The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines [J].

Adams, H ;

Anderson, JC ;

Peace, S ;

Pennell, AMK .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9932-9934

[2] A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates [J].

Ahn, JH ;

Joung, MJ ;

Yoon, NM ;

Oniciu, DC ;

Katritzky, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :488-492

[3]

Baer H.H., 1970, CHEM NITRO NITROSO 2, P75

[4] Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].

Ballini, R ;

Petrini, M .

TETRAHEDRON, 2004, 60 (05) :1017-1047

[5] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[6] THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .21. THE FE(III)-CATALYZED AND THE CU(II)-CATALYZED OXIDATION OF SATURATED-HYDROCARBONS BY HYDROGEN-PEROXIDE - A COMPARATIVE-STUDY [J].

BARTON, DHR ;

BEVIERE, SD ;

CHAVASIRI, W ;

CSUHAI, E ;

DOLLER, D .

TETRAHEDRON, 1992, 48 (14) :2895-2910

[7] The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes [J].

Basavaiah, D ;

Sharada, DS ;

Kumaragurubaran, N ;

Reddy, RM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7135-7137

[8] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[9] Organocatalyzed solvent-free aza-Henry reaction:: A breakthrough in the one-pot synthesis of 1,2-diamines [J].

Bernardi, L ;

Bonini, BF ;

Capitò, E ;

Dessole, G ;

Comes-Franchini, M ;

Fochi, M ;

Ricci, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8168-8171

[10] Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides [J].

Black, DA ;

Arndtsen, BA .

ORGANIC LETTERS, 2004, 6 (07) :1107-1110

← 1 2 3 4 5 6 7 8 9 →