A Simple and Efficient Synthesis of Tertiary Alcohols via Ta2O5- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids

doi:10.6023/cjoc201602025

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2456-2462.DOI: 10.6023/cjoc201602025 Previous Articles Next Articles

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一种简便高效的Ta₂O₅催化溴代芳烃和芳酸的Barbier-Grignard反应制备三级醇

王华然, 唐渝, 杨骏, 张渊明

暨南大学生命科学技术学院化学系广州 510632

收稿日期:2016-02-24 修回日期:2016-05-03 发布日期:2016-06-01
通讯作者: 唐渝,E-mail:tytang@jnu.edu.cn;张渊明,E-mail:tzhangym@jnu.edu.cn 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.

A Simple and Efficient Synthesis of Tertiary Alcohols via Ta₂O₅- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids

Wang Huaran, Tang Yu, Yang Jun, Zhang Yuanming

Department of Chemistry, Jinan University, Guangzhou 510632

Received:2016-02-24 Revised:2016-05-03 Published:2016-06-01
Supported by:
Project supported by the National Natural Science Foundation of China (No.21276104).

1. A Simple and Efficient Synthesis of Tertiary Alcohols via Ta₂O₅- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids.PDF(1333KB)

Abstract

Carried out in THF-toluene at 103℃, the first one-pot Barbier-Grignard reaction to synthesize tertiary alcohols has been developed and systematically investigated using aromatic acids and unactivated aryl bromides in the presence of 10 mol% of Ta₂O₅. A wide range of substituted tertiary alcohols were obtained in moderate to good yields of 48%~87%. Steric and electronic effects of reactants on the reaction have been discussed. A possible mechanism catalyzed by Ta₂O₅ is proposed.

Key words: aryl acid, barbier-grignard-type reaction, synthesis, tertiary alcohol

Cite this article

Wang Huaran, Tang Yu, Yang Jun, Zhang Yuanming. A Simple and Efficient Synthesis of Tertiary Alcohols via Ta₂O₅- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids[J]. Chin. J. Org. Chem., 2016, 36(10): 2456-2462.

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一种简便高效的Ta₂O₅催化溴代芳烃和芳酸的Barbier-Grignard反应制备三级醇

A Simple and Efficient Synthesis of Tertiary Alcohols via Ta₂O₅- Catalyzed Barbier-Grignard Addition of Unactivated Aryl Bromides to Aryl Acids

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一种简便高效的Ta2O5催化溴代芳烃和芳酸的Barbier-Grignard反应制备三级醇