Tris(biphenyl-4-yl)silyl-endcapped polyynes

被引：34

作者：

Chalifoux, Wesley A. ^{[1
]}

Ferguson, Michael J.

Tykwinski, Rik R.

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

[2] Univ Alberta, Dept Chem, Xray Crystallog Lab, Edmonton, AB T6G 2G2, Canada

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 06期

关键词：

polyynes; alkynes; hay coupling; Cadiot-Chodkiewicz coupling; ethynylsilanes; alkyne protecting groups;

D O I：

10.1002/ejoc.200600878

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of tris(tiphenyl-4-yl)silyl (TBPS) as a large protecting group for polyynes has been investigated. The basic building block, TBPS-C C-TMS (1), is synthesized in a new "one-pot" reaction through the sequential addition of lithiated nucleophiles to tetrachlorosilane. The TMS group of differentially protected 1 and the diyne 5 can be selectively removed in the presence of the TBPS group under mild conditions, allowing for the formation of TBPS-endcapped diand tetraynes (3 and 9) by oxidative homocoupling. For the triyne, TBPS-(C C)(3)-TMS (11), chemoselectivity for desilylation decreases dramatically, preventing formation of the corresponding hexayne. X-ray crystallographic analysis of 3 confirms a diameter of 20 A for the TBPS group. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：1001 / 1006

页数：6

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