Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids

被引:42
作者
Cartwright, Kaitie C. [1 ]
Lang, Simon B. [1 ]
Tunge, Jon A. [1 ]
机构
[1] Univ Kansas, Dept Chem, 2010 Malott Hall,1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
基金
美国国家科学基金会;
关键词
ELECTRON-TRANSFER OXIDATION; ALKYL RADICALS; ISOMERIZATION; HYDROAMINATION; ALKENES; REDUCTION; AMIDES; ALLYLAMIDES; RUTHENIUM; AMINATION;
D O I
10.1021/acs.joc.9b00167
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.
引用
收藏
页码:2933 / 2940
页数:8
相关论文
共 51 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   ALKENES FROM ACIDS BY OXIDATIVE DECARBOXYLATION [J].
BACHA, JD ;
KOCHI, JK .
TETRAHEDRON, 1968, 24 (05) :2215-&
[3]   SYNTHESIS OF ENAMIDES [J].
BRETTLE, R ;
MOSEDALE, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2185-2195
[4]   Enamides: valuable organic substrates [J].
Carbery, David R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460
[5]   Decarboxylative Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual Catalysis [J].
Cartwright, Kaitie C. ;
Tunge, Jon A. .
ACS CATALYSIS, 2018, 8 (12) :11801-11806
[6]   Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of -Oxo Acids [J].
Chu, Lingling ;
Lipshultz, Jeffrey M. ;
MacMillan, David W. C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (27) :7929-7933
[7]   Ynamides: A Modern Functional Group for the New Millennium [J].
DeKorver, Kyle A. ;
Li, Hongyan ;
Lohse, Andrew G. ;
Hayashi, Ryuji ;
Lu, Zhenjie ;
Zhang, Yu ;
Hsung, Richard P. .
CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106
[8]   OXIDATION OF FREE RADICALS BY METAL IONS [J].
DELAMA.H ;
KOCHI, JK ;
RUST, FF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (08) :2013-&
[9]   Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes [J].
Evano, Gwilherm ;
Gaumont, Annie-Claude ;
Alayrac, Carole ;
Wrona, Iwona E. ;
Giguere, Joshua R. ;
Delacroix, Olivier ;
Bayle, Alexandre ;
Jouvin, Kevin ;
Theunissen, Cedric ;
Gatignol, Jeremie ;
Silvanus, Andrew C. .
TETRAHEDRON, 2014, 70 (08) :1529-1616
[10]  
FLITSCH W, 1975, SYNTHESIS-STUTTGART, P685