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Synthesis 2013; 45(3): 341-346
DOI: 10.1055/s-0032-1317946
DOI: 10.1055/s-0032-1317946
paper
A Stereoselective Approach to (Z)-1-Silyl-2-aryl-1,3-dienes from 4-(Phenylselanyl)but-1-yne via Palladium-Catalyzed Silylstannylation and Selenoxide Elimination
Further Information
Publication History
Received: 08 November 2012
Accepted after revision: 03 December 2012
Publication Date:
03 January 2013 (online)
Abstract
The palladium-catalyzed silylstannylation of 4-(phenylselanyl)but-1-yne proceeded regio- and stereoselectively, followed by selenoxide elimination via oxidation to give (Z)-1-(trimethylsilyl)-2-(tributylstannyl)buta-1,3-diene in good yield. This conjugated diene underwent the Stille coupling reaction with various aryl iodides in the presence of Pd(PPh3)4 to afford (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes with high stereoselectivity. Reversing the order of selenoxide elimination and Stille coupling reaction in the synthetic procedure also resulted in good yields of (Z)-2-aryl-1-(trimethylsilyl)buta-1,3-dienes.
Key words
silylstannylation - selenide - Stille coupling reaction - selenoxide elimination - conjugated dienes - stereoselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For synthesis of natural products via palladium-catalyzed silylstannylation, see ref. 7 and: