Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones

TETRAHEDRON LETTERS

卷:52

Article

Taylor, Jason G.²  Ribeiro, Rodrigo da Silva¹  Correia, Carlos Roque D.¹ 

[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084971 Sao Paulo, Brazil

[2] Univ Fed Ouro Preto, ICEB, Dept Quim, BR-35400000 Ouro Preto, MG, Brazil

关键词: Arenediazonium tetrafluoroborates;    Heck-Matsuda;    Arylation;    3,3-Diarylacrylates;    Palladium;    Indanones;   

DOI  :  10.1016/j.tetlet.2011.05.039

来源: Elsevier

【 摘 要 】

A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)(2) as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

Free