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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 13
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Original Articles

Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Selenium via Hydrozirconation of (Z)-3-(Trimethylsilyl)alk-3-en-1-ynes

, , &
Pages 2378-2391 | Received 30 Sep 2008, Published online: 01 Jun 2009
 

Abstract

Sonogashira coupling of (E)-α-iodovinylsilanes 1 with (trimethylsilyl)-acetylene gave (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-ynes 2, which underwent a desilylation reaction to afford (Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3 in good yields. (1E,3Z)-1-Arylseleno-3-(trimethylsilyl)-substituted 1,3-dienes 5 could be synthesized stereoselectively via hydrozirconation of (Z)-3-(trimethylsilyl)alk-3-en-1-ynes 3, followed by trapping with arylselenenyl bromides.

ACKNOWLEDGMENTS

We thank the National Natural Science Foundation of China (Project No. 20462002) and the Natural Science Foundation of Jiangxi Province (Project No. 2007GZW0172) for financial support.

Notes

a The reaction of 1 (2 mmol) with (trimethylsilyl)acetylene (3 mmol) was carried out using Pd(PPh3)4 (0.1 mmol), CuI (0.2 mmol), and piperidine (6 mL) at room temperature for 2 h.

b The desilylation reaction of 2 (1 mmol) with KF (10 mmol) was performed in methanol (4 mL) at 70°C for 5 h.

c Isolated yield of 2 based on the 1 used.

a Isolated yield based on the 3 used.

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