十钨酸盐光催化偶氮苯与N,N-二甲基酰胺的氢氨甲基化反应

Decatungstate-Photocatalyzed Hydroamidomethylation of Azobenzenes with ,-Dimethylamides.

作者信息

Yang Jingya, Wang Cunhui, Han Yating, Huang Bao, Mei Shouying, Chen Dong-Ping, Zhou Hongyan

机构信息

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, People's Republic of China.

College of Science, Gansu Agricultural University, Lanzhou, Gansu 730070, People's Republic of China.

出版信息

Org Lett. 2024 Nov 29;26(47):10165-10169. doi: 10.1021/acs.orglett.4c03931. Epub 2024 Nov 19.

DOI:10.1021/acs.orglett.4c03931

PMID:39561349

Abstract

A photocatalytic hydroamidomethylation of azobenzenes with ,-dimethylamides has been developed. Using tetrabutylammonium decatungstate (TBADT) as a photocatalyst, an array of azobenzenes and ,-dimethylamides reacted smoothly under visible light irradiation, affording previously unreported -amidomethyl-,'-diarylhydrazines in generally high yields. Mechanistic studies indicate that the reaction is enabled by TBADT-mediated hydrogen atom transfer (HAT) photocatalysis. This work is fundamentally different from the previously reported reaction of ,-dimethylformamide with azobenzenes.

摘要

已开发出一种用α,β-二甲基酰胺对偶氮苯进行光催化氢酰胺甲基化反应。以四丁基铵十钨酸盐（TBADT）作为光催化剂，一系列偶氮苯和α,β-二甲基酰胺在可见光照射下顺利反应，通常以高产率得到此前未报道的α-酰胺甲基-α',β'-二芳基肼。机理研究表明，该反应是由TBADT介导的氢原子转移（HAT）光催化实现的。这项工作与之前报道的α,β-二甲基甲酰胺与偶氮苯的反应在本质上不同。