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Radical‐Induced Metal‐Free Alkynylation of Aldehydes by Direct CH Activation
Author(s) -
Liu Xuesong,
Yu Linqian,
Luo Mupeng,
Zhu Jidong,
Wei Wanguo
Publication year - 2015
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.201501094
Subject(s) - hypervalent molecule , alkynylation , reagent , chemistry , aldehyde , substrate (aquarium) , triple bond , metal , iodine , combinatorial chemistry , medicinal chemistry , organic chemistry , double bond , catalysis , oceanography , geology
A direct C(sp 2 )H alkynylation of aldehyde C(O)H bonds with hypervalent iodine alkynylation reagents provides ynones under metal‐free conditions. In this method, 1‐[(triisopropylsilyl)ethynyl]‐1,2‐benziodoxol‐3(1 H )‐one (TIPS‐EBX) constitutes an efficient alkynylation reagent for the introduction of the triple bond. The substrate scope is extended to a variety of (hetero)aromatic, aliphatic, and α,β‐unsaturated aldehydes.