Synthesis of dithieno[2,3-b:4',3'-d]siloles and their selective bromination

The Journal of Organic Chemistry
Jincan ZhaoHua Wang

Abstract

The efficient synthesis of novel unsymmetrical dithienosiloles, 7,7-dimethyl-4,6-di(trimethylsilyl)-dithieno[2,3-b:4',3'-d]silole (1) and 7,7-dimethyl-2,4,6-tri(trimethylsilyl)-dithieno[2,3-b:4',3'-d]silole (2) has been developed by intramolecular silole formation with 4,4'-dibromo-2,2',5,5'-tetrakis(trimethylsilyl)-[3,3']bithienyl (3) as the starting material in the presence of t-BuLi. Upon treatment with N-bromosuccinimide (NBS) under controlled conditions, dithieno[2,3-b:4',3'-d]silole was selectively brominated to produce mono-, di-, and tribrominated dithieno[2,3-b:4',3'-d]siloles in good yields. The crystal structures of the title compounds are described.

References

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Mar 25, 2011·Chemical Communications : Chem Comm·Young-Rae HongZhi-Kuan Chen

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Citations

May 21, 2016·Chemical Reviews·Indranirekha SaikiaProdeep Phukan
Mar 1, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Lu LiHua Wang
Nov 7, 2012·Journal of the American Chemical Society·Masahiro OnoeNaoto Chatani

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