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Direct Synthesis of α‐Allenols from TMS‐Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride
Author(s) -
Huang Xiaojun,
Bugarin Alejandro
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603250
Subject(s) - tetrabutylammonium fluoride , tetrabutylammonium hydroxide , fluoride , adduct , chemistry , hydroxide , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry
A unique chemoselective synthesis of α‐allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well‐tolerated in this reaction, while affording adducts in moderate to excellent yields (48–96 %, average 76 %). Mechanistic studies, including the use of tetrabutylammonium hydroxide (TBAH), revealed that the hydroxide ion can be the responsible for the observed rearrangement.