Novel synthesis of 2-oxo-3-butynoates by copper-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride
- PMID: 14682719
- DOI: 10.1021/jo0353076
Novel synthesis of 2-oxo-3-butynoates by copper-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride
Abstract
A general and efficient Cu(I)-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride for the synthesis of 2-oxo-3-butynoates and 2-oxo-3-butynoamides was developed. Readily available starting materials, the mild reaction conditions, wide functional group tolerance, and the obviation of stoichiometric organolithium or magnesium reagents combine to highlight this reaction.
Similar articles
-
Cross-coupling reaction of alkyl halides with grignard reagents catalyzed by Ni, Pd, or Cu complexes with pi-carbon ligand(s).Acc Chem Res. 2008 Nov 18;41(11):1545-54. doi: 10.1021/ar800138a. Acc Chem Res. 2008. PMID: 18973349
-
Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions.J Org Chem. 2005 May 27;70(11):4393-6. doi: 10.1021/jo0503310. J Org Chem. 2005. PMID: 15903317
-
Synthesis of polyfunctional allenes by successive copper-mediated substitutions.Chemistry. 2011 Apr 4;17(15):4232-7. doi: 10.1002/chem.201003273. Epub 2011 Mar 7. Chemistry. 2011. PMID: 21384450
-
Gold-catalyzed highly efficient access to 3(2H)-furanones from 2-oxo-3-butynoates and related compounds.Org Lett. 2006 Aug 3;8(16):3445-8. doi: 10.1021/ol061059z. Org Lett. 2006. PMID: 16869631
-
Palladium-based catalytic systems for the synthesis of conjugated enynes by sonogashira reactions and related alkynylations.Angew Chem Int Ed Engl. 2007;46(6):834-71. doi: 10.1002/anie.200602761. Angew Chem Int Ed Engl. 2007. PMID: 17335070 Review.
Cited by
-
A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.Org Lett. 2012 Jan 20;14(2):510-2. doi: 10.1021/ol203093g. Epub 2011 Dec 23. Org Lett. 2012. PMID: 22195730 Free PMC article.
-
Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.J Org Chem. 2014 May 2;79(9):4167-73. doi: 10.1021/jo500365h. Epub 2014 Apr 18. J Org Chem. 2014. PMID: 24724797 Free PMC article.
LinkOut - more resources
Full Text Sources