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Thiophenol‐Mediated 1,5‐Hydrogen Atom Abstraction: Easy Access to Mono‐ and Bicyclic Compounds
Author(s) -
Beaufils Florent,
Dénès Fabrice,
Becattini Barbara,
Renaud Philippe,
Schenk Kurt
Publication year - 2005
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.200505211
Subject(s) - thiophenol , bicyclic molecule , chemistry , cyclopentane , hydrogen atom abstraction , moiety , hydrogen atom , surface modification , intermolecular force , triple bond , combinatorial chemistry , stereochemistry , medicinal chemistry , hydrogen , organic chemistry , double bond , molecule , alkyl
A thiophenol‐mediated method for cyclization of alkynes is described. The reaction cascade involves the intermolecular addition of a phenylthiyl radical to a terminal triple bond generating an alkenyl radical, followed by a 1,5‐hydrogen atom transfer and a 5‐ exo‐ trig radical cyclization. This very efficient tin‐free procedure allows one to prepare highly functionalized cyclopentane derivatives as well as fused bicyclic and spirocyclic compounds from easily available precursors. During this cyclization process, a phenylthio moiety is incorporated into the final cyclized products. This functionalization is particularly attractive for further transformation of the products.