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16 Sep 18:27

A reaction used by chemists worldwide goes green

Nature, Published online: 13 September 2019; doi:10.1038/d41586-019-02717-y

Thanks to a catalyst, a crucial chemical process no longer requires an explosive ingredient.
30 Apr 00:52

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

by Xuesong Liu, Linqian Yu, Mupeng Luo, Jidong Zhu, Wanguo Wei

Abstract

A direct C(sp2)[BOND]H alkynylation of aldehyde C(O)[BOND]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.

Thumbnail image of graphical abstract

Direct C(sp2)[BOND]H activation of aldehyde C(O)[BOND]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.