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Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs
Author(s) -
LujanMontelongo J. Armando,
Estevez Angel Ojeda,
Fleming Fraser F.
Publication year - 2015
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.201403615
Subject(s) - chemistry , nucleophile , alkyl , combinatorial chemistry , organic chemistry , catalysis
Alkyl sulfinates function as formal nucleophiles in Mannich‐type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two‐step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.