Synlett 2013; 24(15): 1953-1958
DOI: 10.1055/s-0033-1339482
letter
© Georg Thieme Verlag Stuttgart · New York

Simple and General Procedure for the Synthesis of α,β-Alkynyl Ketones from Nitriles Using Alkynyldimethylaluminum Reagents

Balaji L. Korbad
Department of Life Chemistry, Catholic University of Daegu, Gyeongsan-si, Gyeongbuk 712-702, Korea   Fax: +82(53)8503728   Email: [email protected]
,
Sang-Hyeup Lee*
Department of Life Chemistry, Catholic University of Daegu, Gyeongsan-si, Gyeongbuk 712-702, Korea   Fax: +82(53)8503728   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 29 May 2013

Accepted after revision: 01 July 2013

Publication Date:
14 August 2013 (online)


Abstract

A simple and efficient approach for the synthesis of α,β-alkynyl ketones from nitriles and alkynyldimethylaluminum reagents, derived from trimethylaluminum and alkynes, is described. This methodology provides access to a wide range of α,β-alkynyl ketones with aliphatic, aromatic, and heteroaromatic substituents in moderate to high yield (53–90%). In the cases of aryl-substituted nitriles, the product can also be obtained as α,β-alkynyl N-H ket­imines in high yield (88–93%).

Supporting Information

 
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