Radical-Induced Metal-Free Alkynylation of Aldehydes by Direct CH Activation

A direct C(sp2)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(1H)‐one (TIPS‐EBX) constitutes an efficient alkynylation reagent for the introduction of...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-06, Vol.21 (24), p.8745-8749
Main Authors: Liu, Xuesong, Yu, Linqian, Luo, Mupeng, Zhu, Jidong, Wei, Wanguo
Format: Article
Language:English
Subjects:
Activation
Aldehydes
Aldehydes - chemistry
Aliphatic compounds
Alkynes - chemistry
alkynylation
Catalysis
CH activation
Free Radicals
hypervalent iodine
Iodides
Iodine
Molecular Structure
radicals
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Summary:A direct C(sp2)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(1H)‐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. Direct C(sp2)H activation of aldehyde C(O)H bonds with hypervalent alkynyl iodides (G‐EBX) provides ynones under metal‐free conditions. 1‐[(Triisopropylsilyl)ethynyl]‐1,2‐benziodoxol‐3(1H)‐one (TIPS‐EBX) constitutes an efficient alkynylation reagent for the introduction of the triple bond.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201501094