Palladium-catalyzed double cross-coupling of E-vinylic dibromides with PhZnCl and the synthesis of tamoxifen

Journal of the Brazilian Chemical Society

Universidade Estadual de Campinas, Campinas, Brazil¹  Robello, Luís Gustavo¹  Pilli, Ronaldo A.¹ 

关键词: (E)-1;    2-vinylic dibromides;    double cross-coupling;    palladium catalysis;    tri- and tetrasubstituted olefins;    tamoxifen;   

DOI  :  10.1590/S0103-50532004000600023

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

(E)-1,2-vinylic dibromides 11a-f were stereoselectively prepared via bromination of acetylenic compounds with pyridinium tribromide in MeOH/CCl4 at low temperature and double cross-coupled with PhZnCl under Pd(0) catalysis (Negishi protocol) to afford tri- and tetrasubstituted olefins 14a-e. Tamoxifen, a selective estrogen receptor modulator clinically prescribed in breast cancer therapy, was prepared in 7 steps and 30% overall yield from 4-iodophenol (3) as a 2.3:1 mixture of (Z)- and (E)-isomers.

【 授权许可】

Unknown