Rhodium-Catalyzed C-H Bond Functionalization with Amides by Double C-H/C-N Bond Activation

被引:181
作者
Meng, Guangrong [1 ]
Szostak, Michal [1 ]
机构
[1] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA
关键词
RH(I)-CATALYZED DIRECT ARYLATION; FORMING REACTIONS; CARBOXYLIC-ACIDS; DECARBONYLATION; NITROGEN; CLEAVAGE; CHLORIDES; ARENES; ALKENYLATION; DERIVATIVES;
D O I
10.1021/acs.orglett.6b00058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first C-H bond functionalization with amides as the coupling partners via selective activation of the amide N-C bond using rhodium(I) catalysts under highly chemoselective conditions is reported. Notably, this report constitutes the first catalytic activation of the amide N-C(O) bond by rhodium. We expect that this concept will have broad implications for using amides as coupling partners for C-H activation beyond the work described herein.
引用
收藏
页码:796 / 799
页数:4
相关论文
共 76 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]  
Ackermann L., 2009, ANGEW CHEM, V121, P207
[3]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[4]   Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901
[5]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[6]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[7]  
[Anonymous], 2010, CHEM REV, V110, P1
[8]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[9]  
Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
[10]   Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].
Berman, Ashley M. ;
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+