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. 2009 May 20;131(19):6668-9.
doi: 10.1021/ja901778y.

Iridium-catalyzed addition of acid chlorides to terminal alkynes

Tomohiro Iwai  1 , Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji
Affiliations

Iridium-catalyzed addition of acid chlorides to terminal alkynes

Tomohiro Iwai et al. J Am Chem Soc. .

Abstract

An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-beta-chloro-alpha,beta-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans.

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