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Sulfination of Alcohols with p ‐Toluenesulfonylmethyl Isocyanide under Metal‐Free Conditions: A Mitsunobu Approach
Author(s) -
Kadari Lingaswamy,
Radha Krishna Palakodety,
Lakshmi Prapurna Y.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600997
Subject(s) - chemistry , diad , isocyanide , triphenylphosphine , reagent , mitsunobu reaction , combinatorial chemistry , organic chemistry , nucleophile , diethyl azodicarboxylate , catalysis , polymer , copolymer
A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal‐free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p ‐toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds.