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

被引：1
作者：
Shintaku, Kazuki [1 ]
Maeda, Hajime [1 ]
Segi, Masahito [1 ]
机构：
[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Sci, Kanazawa, Ishikawa 9201192, Japan
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 03期
关键词：
silylstannylation; selenide; Stille coupling reaction; selenoxide elimination; conjugated dienes; stereoselectivity; ORGANIC-SYNTHESIS; SILASTANNATION; SILICON; ALKYNES; FUNCTIONALIZATION; SILYLSTANNANES; ACETYLENES; PRECURSORS; CONVERSION; CHEMISTRY;
D O I：
10.1055/s-0032-1317946
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：341 / 346
页数：6
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