Photocatalyst-free hypervalent iodine reagent catalyzed decarboxylative acylarylation of acrylamides with α-oxocarboxylic acids driven by visible-light irradiation

被引:140
作者
Ji, Wangqin [1 ]
Tan, Hui [1 ]
Wang, Min [1 ]
Li, Pinhua [1 ]
Wang, Lei [1 ,2 ]
机构
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
HIGHLY EFFICIENT ACCESS; ACTIVATED ALKENES; N-ARYLACRYLAMIDES; ROOM-TEMPERATURE; PHOTOREDOX CATALYSIS; CARBOXYLIC-ACIDS; ORTHO-ACYLATION; C-C; H FUNCTIONALIZATION; C(SP(3))-H BONDS;
D O I
10.1039/c5cc08253f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A hypervalent iodine(III) reagent catalyzed carbonylarylation of acrylamides with alpha-oxocarboxylic acids driven by visible-light without a photoredox catalyst has been developed. The reactions generate the corresponding products in good yields at room temperature. Experiments indicate that a blue LED (450-455 nm) is the most effective energy for the cleavage of the oxygen-iodine bond to initiate the reaction. Mechanistic studies further demonstrate that the reaction undergoes a cascade decarboxylative radical addition/cyclization process along with releasing CO2 and H-2.
引用
收藏
页码:1462 / 1465
页数:4
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