Radical-Induced Metal-Free Alkynylation of Aldehydes by Direct CH Activation

Radical-Induced Metal-Free Alkynylation of Aldehydes by Direct CH 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 t...

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Veröffentlicht in:Chemistry : a European journal 2015-06, Vol.21 (24), p.8745
Hauptverfasser: Liu, Xuesong, Yu, Linqian, Luo, Mupeng, Zhu, Jidong, Wei, Wanguo
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
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Zusammenfassung: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 [alpha],[beta]-unsaturated aldehydes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201501094