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Nucleophilic gem ‐Difluoro(phenylsulfanyl)methylation of Carbonyl Compounds with PhSCF 2 H in the Presence of a Phosphazene as a Base
Author(s) -
Punirun Teerachai,
Soorukram Darunee,
Kuhakarn Chutima,
Reutrakul Vichai,
Pohmakotr Manat
Publication year - 2014
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.201402162
Subject(s) - chemistry , phosphazene , nucleophile , nucleophilic addition , base (topology) , adduct , electrophile , medicinal chemistry , methylation , organic chemistry , catalysis , dna , mathematical analysis , biochemistry , polymer , mathematics
Direct nucleophilic gem ‐difluoro(phenylsulfanyl)methylation of carbonyl compounds has been achieved by use of difluoro(phenylsulfanyl)methane (PhSCF 2 H) and the phosphazene base P 4 ‐ t Bu in THF. Non‐enolizable aldehydes and ketones are suitable substrates to undergo nucleophilic gem ‐difluoro(phenylsulfanyl)methylation, providing α‐ gem ‐difluoromethylated adducts in good yields. In addition, this methodology is also applicable with cyclic imides and acid anhydrides.