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Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o ‐Alkynylaryl Weinreb Amides
Author(s) -
Phetcharawetch Jongkonporn,
Betterley Nolan M.,
Soorukram Darunee,
Pohmakotr Manat,
Reutrakul Vichai,
Kuhakarn Chutima
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701322
Subject(s) - chemistry , medicinal chemistry , trimethylsilane , nucleophilic addition , benzoic acid , amide , nucleophile , organic chemistry , halogenation , tandem , ketone , catalysis , materials science , composite material
[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF 2 SiMe 3 ) underwent a fluoride‐induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were converted into difluoromethyl ketones through selective reductive cleavage of the phenylsulfanyl group. The reaction of o ‐alkynyl Weinreb amides derived from benzoic acid derivatives resulted in the formation of cyclized products through a 5‐ exo ‐ dig cyclization.