Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes

doi:10.6023/cjoc201506025

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2545-2551.DOI: 10.6023/cjoc201506025 Previous Articles Next Articles

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铋(III)催化Barbier-Grignard-Type溴代芳香烃和醛的反应

温运明, 陈桂芳, 唐渝, 陈静, 杨骏, 张渊明

暨南大学化学系广州 510632

收稿日期:2015-06-18 修回日期:2015-08-25 发布日期:2015-08-31
通讯作者: 唐渝, 张渊明 E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
基金资助:
国家自然科学基金(No. 21276104)资助项目.

Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes

Wen Yunming, Chen Guifang, Tang Yu, Chen Jing, Yang Jun, Zhang Yuanming

Department of Chemistry, Jinan University, Guangzhou 510632

Received:2015-06-18 Revised:2015-08-25 Published:2015-08-31
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21276104).

1. Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes.PDF(956KB)

Abstract

A highly versatile and efficient method has been developed for the Barbier-Grignard-type arylation and alkylation of aldehydes using unactivated bromides and Mg in tetrahydrofuran at 65 ℃ promoted by BiCl₃ and PPh₃. This method has offered high yields of 61%~99% mostly, mild reaction conditions, short reaction time, easy workup and a one-pot procedure. The steric, electronic effects and some new results have been discussed. A possible mechanism catalyzed by BiCl₃ and Ph₃P was reasonably proposed.

Key words: secondary alcohol, Barbier-Grignard-type reaction, one-pot, aldehyde, BiCl₃

Cite this article

Wen Yunming, Chen Guifang, Tang Yu, Chen Jing, Yang Jun, Zhang Yuanming. Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes[J]. Chin. J. Org. Chem., 2015, 35(12): 2545-2551.

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铋(III)催化Barbier-Grignard-Type溴代芳香烃和醛的反应

Effective Bismuth(III)-Promoted Barbier-Grignard-Type Reactions of Bromides with Aldehydes

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