One-Pot Synthesis of Trisubstituted Conjugated Dienes via Sequential Suzuki−Miyaura Cross-Coupling with Alkenyl- and Alkyltrifluoroborates

The sequential, stereoselective disubstitution of 1,1-dibromoalkenes using a variety of alkenyltrifluoroborates followed by alkyltrifluoroborates in the presence of Pd(PPh3)4 is described. This synthetic method proceeds smoothly in one pot under mild reaction conditions to provide the corresponding...

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Veröffentlicht in:	Journal of organic chemistry 2006-03, Vol.71 (6), p.2493-2498
Hauptverfasser:	Molander, Gary A, Yokoyama, Yasuo
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkadienes - chemical synthesis Alkadienes - chemistry Alkenes - chemistry Borates - chemistry Chemistry Exact sciences and technology Molecular Structure Organic chemistry Stereoisomerism
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container_end_page	2498
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container_title	Journal of organic chemistry
container_volume	71
creator	Molander, Gary A Yokoyama, Yasuo
description	The sequential, stereoselective disubstitution of 1,1-dibromoalkenes using a variety of alkenyltrifluoroborates followed by alkyltrifluoroborates in the presence of Pd(PPh3)4 is described. This synthetic method proceeds smoothly in one pot under mild reaction conditions to provide the corresponding trisubstituted, conjugated dienes in excellent yield. Moreover, the method is operationally very simple because the organotrifluoroborates are stable in air, and the byproducts are innocuous inorganic salts.
doi_str_mv	10.1021/jo052636k
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subjects	Alkadienes - chemical synthesis Alkadienes - chemistry Alkenes - chemistry Borates - chemistry Chemistry Exact sciences and technology Molecular Structure Organic chemistry Stereoisomerism
title	One-Pot Synthesis of Trisubstituted Conjugated Dienes via Sequential Suzuki−Miyaura Cross-Coupling with Alkenyl- and Alkyltrifluoroborates
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