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

An 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...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 365; no. 24; pp. 4507 - 4512
Main Authors Shen, Zheng‐Jia, Tu, Jia‐Lin, Guo, Lin, Yang, Chao, Xia, Wujiong
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 19.12.2023
Wiley Subscription Services, Inc
Subjects
Aldehydes
Amides
bromodifluoroamides
Chemical reduction
Chemistry
Chemistry, Applied
Chemistry, Organic
electron reductive umpolung
Electrosynthesis
Functional groups
Ketones
Physical Sciences
Reagents
Reformatsky reaction
Science & Technology
Substrates
Transition metals
β-hydroxy-α,α-difluoro amides
NOZAKI-HIYAMA ALLYLATION
Reformatsky reaction
BETA-HYDROXY ESTERS
CATALYZED AMINODIFLUOROALKYLATION
electron reductive umpolung
beta-hydroxy-alpha,alpha-difluoro amides
KETONES
Electrosynthesis
FLUORINE
LACTAMS
STEREOGENIC CENTERS
EFFICIENT
ACCESS
CYCLIZATION
bromodifluoroamides
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Summary:An 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301028