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
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
[21]   Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates [J].
DeBoef, B ;
Pastine, SJ ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6556-6557
[22]  
Doye S, 2001, ANGEW CHEM INT EDIT, V40, P3351, DOI 10.1002/1521-3773(20010917)40:18<3351::AID-ANIE3351>3.0.CO
[23]  
2-B
[24]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[25]  
2-6
[26]  
Fässler R, 2002, ANGEW CHEM INT EDIT, V41, P3054, DOI 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO
[27]  
2-B
[28]   Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex [J].
Fischer, C ;
Carreira, EM .
ORGANIC LETTERS, 2001, 3 (26) :4319-4321
[29]   Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].
Frantz, DE ;
Fässler, R ;
Carreira, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246
[30]   Asymmetric catalysis of the Friedel-Crafts reaction with fluoral by chiral binaphthol-derived titanium catalysts through asymmetric activation [J].
Ishii, A ;
Soloshonok, VA ;
Mikami, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1597-1599