文献类型：期刊文献

英文题名：Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

作者：Huang, He[1];Li, Xiangmin[1,2,3];Yu, Chenguang[1];Zhang, Yueteng[1];Mariano, Patrick S.[1];Wang, Wei[1,2,3]

机构：[1]Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA;[2]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, 130 Mei Long Rd, Shanghai 200237, Peoples R China

年份：2017

卷号：56

期号：6

起止页码：1500

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20170203234721);WOS:【SCI-EXPANDED(收录号:WOS:000394998300007)，CCR-EXPANDED(收录号:WOS:000394998300007)】；

基金：Support of this research by the ACS-PRF (57164-ND1), the NSF (CHE-1565085), and the National Science Foundation of China (21372073 and 21572055) is gratefully acknowledged.

语种：英文

外文关键词：flow chemistry; formylation; nickel catalysis; photoredox catalysis; synthetic methods

摘要：A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial insitu generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.