Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage

被引:20
作者
Cheng, Guolin [1 ]
Lv, Weiwei [1 ]
Kuai, Changsheng [1 ]
Wen, Si [1 ]
Xiao, Shangyun [1 ]
机构
[1] Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
关键词
ALPHA-KETO ACIDS; CONJUGATED YNONES; DECARBOXYLATIVE AMIDATION; CASCADE REACTION; ALKYNYL IMINES; TRIPLE BOND; ACTIVATION; DECARBONYLATION; ALDEHYDES; ACCESS;
D O I
10.1039/c7cc09310a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new protocol for the synthesis of amides via base-promoted cleavage of the C(sp)-C(CO) bond of ynones with aliphatic primary and secondary amines under transition-metal-, ligand-, and oxidant-free conditions has been developed. This method exhibits a wide substrate scope, high functional group tolerance and exclusive chemoselectivity, as well as mild reaction conditions.
引用
收藏
页码:1726 / 1729
页数:4
相关论文
共 36 条
[21]   H2O2-mediated oxidative formation of amides from aromatic amines and 1,3-diketones as acylation agents via C-C bond cleavage at room temperature in water under metal-free conditions [J].
Sun, Xi ;
Wang, Min ;
Li, Pinhua ;
Zhang, Xiuli ;
Wang, Lei .
GREEN CHEMISTRY, 2013, 15 (12) :3289-3294
[22]   Facile Access to Chiral Ketones through Metal-Free Oxidative C?C Bond Cleavage of Aldehydes by O2 [J].
Tiwari, Bhoopendra ;
Zhang, Junmin ;
Chi, Yonggui Robin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) :1911-1914
[23]   Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones [J].
Verma, Ajay ;
Kumar, Sangit .
ORGANIC LETTERS, 2016, 18 (17) :4388-4391
[24]   Direct Approaches to Nitriles via Highly Efficient Nitrogenation Strategy through C-H or C-C Bond Cleavage [J].
Wang, Teng ;
Jiao, Ning .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) :1137-1145
[25]   A General Synthesis of Ynones from Aldehydes via Oxidative C-C bond Cleavage under Aerobic Conditions [J].
Wang, Zhaofeng ;
Li, Li ;
Huang, Yong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (35) :12233-12236
[26]   Controlled Rh-Catalyzed Mono- and Double-decarbonylation of Alkynyl α-Diones To Form Conjugated Ynones and Disubstituted Alkynes [J].
Whittaker, Rachel E. ;
Dong, Guangbin .
ORGANIC LETTERS, 2015, 17 (21) :5504-5507
[27]   Distal-Bond-Selective C-C Activation of Ring-Fused Cyclopentanones: An Efficient Access to Spiroindanones [J].
Xia, Ying ;
Wang, Jianbo ;
Dong, Guangbin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) :2376-2380
[28]   Catalytic activation of carbon-carbon bonds in cyclopentanones [J].
Xia, Ying ;
Lu, Gang ;
Liu, Peng ;
Dong, Guangbin .
NATURE, 2016, 539 (7630) :546-550
[29]   Reaction of Frustrated Lewis Pairs with Conjugated Ynones-Selective Hydrogenation of the Carbon-Carbon Triple Bond [J].
Xu, Bao-Hua ;
Kehr, Gerald ;
Froehlich, Roland ;
Wibbeling, Birgit ;
Schirmer, Birgitta ;
Grimme, Stefan ;
Erker, Gerhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7183-7186
[30]   Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines [J].
Xu, Wen-Tao ;
Huang, Bei ;
Dai, Jian-Jun ;
Xu, Jun ;
Xu, Hua-Jian .
ORGANIC LETTERS, 2016, 18 (13) :3114-3117