Iridium-Catalyzed Addition of Acid Chlorides to Terminal Alkynes
- 22 April 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 131 (19) , 6668-6669
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)-β-chloro-α,β-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.Keywords
This publication has 19 references indexed in Scilit:
- Rhodium-Complex-Catalyzed Addition Reactions of Chloroacetyl Chlorides to AlkynesOrganic Letters, 2008
- Rhodium-Catalyzed Regioselective C−H Functionalization via Decarbonylation of Acid Chlorides and C−H Bond Activation under Phosphine-Free ConditionsJournal of the American Chemical Society, 2008
- Rhodium‐Catalyzed Nondecarbonylative Addition Reaction of ClCOCOOC2H5 to AlkynesChemistry – A European Journal, 2005
- CO-Retentive Addition Reactions of Fluorinated Acid Chlorides to AlkynesOrganic Letters, 2005
- Rhodium‐Catalyzed Mizoroki–Heck‐Type Arylation of Alkenes with Aroyl Chlorides under Phosphane‐ and Base‐Free ConditionsAngewandte Chemie International Edition, 2003
- The First Example of Rhodium(I)-Catalyzed Regio- and Stereoselective Chloroesterification of Alkynes with Chloroformate EstersJournal of the American Chemical Society, 1998
- Rhodium-Catalyzed Reaction of Aroyl Chlorides with AlkynesThe Journal of Organic Chemistry, 1996
- 1,4-Carbosilylation of 1,3-Dienes via Palladium Catalyzed Three-Component Coupling ReactionJournal of the American Chemical Society, 1995
- A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladiumJournal of the American Chemical Society, 1978
- The Synthesis of Some α,β-Unsaturated Aldehydes1Journal of the American Chemical Society, 1950