Electroreductive Umpolung Enabling Reformatsky‐Type Reaction of Bromodifluoroamides with Aldehydes/Ketones

Author:

Shen Zheng‐Jia1,Tu Jia‐Lin1,Guo Lin1,Yang Chao1,Xia Wujiong12ORCID

Affiliation:

1. State Key Lab of Urban Water Resource and Environment School of Science Harbin Institute of Technology (Shenzhen) Shenzhen 518055 People's Republic of China

2. School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China

Abstract

AbstractAn electrochemical Reformatsky‐type reaction of bromodifluoroamides with aldehydes/ketones via electron reductive umpolung is reported, leading to the generation of a series of β‐hydroxy‐α,α‐difluoro amides in moderate to good yields. This protocol tolerated a variety of commercially available alkyl ketone, alkyl and aromatic aldehydes, featuring broad substrate scope and good functional group tolerance under transition metal‐free conditions without metal reduction reagents. Control experiment indicated that the reaction proceeded via an electron reductive umpolung pathway.

Funder

Shenzhen Graduate School, Peking University

Natural Science Foundation of Guangdong Province

Basic and Applied Basic Research Foundation of Guangdong Province

Publisher

Wiley

Subject

General Chemistry

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