Radical-induced metal-free alkynylation of aldehydes by direct C-H activation.
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(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.
Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210 (P. R. China).
Xuesong
X
Liu
Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210 (P. R. China).
Linqian
L
Yu
Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210 (P. R. China).
Mupeng
M
Luo
Interdisciplinary Research Center on Biology and Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Lingling Road, Shanghai 200032 (P. R. China). zhujd@sioc.ac.cn.
Jidong
J
Zhu
Shanghai Advanced Research Institute, Chinese Academy of Sciences, 99 Haike Road, Shanghai 201210 (P. R. China). weiwg@sari.ac.cn.
Wanguo
W
Wei
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005609:Free Radicals; D015394:Molecular Structure
D000447:Aldehydes; D000480:Alkynes; D005609:Free Radicals
CH activation; aldehydes; alkynylation; hypervalent iodine; radicals