Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)-N Bond Cleavage

被引：6

作者：

Shiozuka, Akira ^{[1
]}

Wu, Di ^{[1
]}

Kawashima, Kyohei ^{[2
]}

Mori, Toshifumi ^{[1
,2
]}

Sekine, Kohei ^{[1
,2
]}

Kuninobu, Yoichiro ^{[1
,2
]}

机构：

[1] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan

来源：

ACS CATALYSIS | 2024年 / 14卷 / 08期

基金：

日本学术振兴会;

关键词：

C-N bond cleavage; carbamoylarylation; aryl migration; alkene; difunctionalization; GENERATION; DIFUNCTIONALIZATION; REARRANGEMENT; SUBSTITUTION; REDUCTION; NITROGEN;

D O I：

10.1021/acscatal.4c00523

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We report carbamoylarylation of alkenes using N-aryl oxamic acid derivatives under visible-light irradiation. Reactions of alkenes with carbamoyl radicals generated using N-aryl oxamic acid derivatives to afford Giese-type products or 3,4-dihydroquinolin-2(1H)-ones via ortho-radical addition to an aryl amide moiety have been previously reported. However, this study reveals that the introduction of a removable bulky group onto the nitrogen atom of N-aryl oxamic acids facilitates the radical addition of carbamoyl radicals to alkenes, resulting in 1,4-aryl migration via C(aryl)-N bond cleavage, thus affording arylpropanamides. Various alkenes, such as acrylic acid and styrene derivatives, are successfully applied to the synthesis of a variety of arylpropanamide derivatives, including 1,4-dicarbonyl amides, forming two C-C bonds.

引用

页码：5972 / 5977

页数：6

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