Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids

doi:10.6023/cjoc202003058

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2086-2093.DOI: 10.6023/cjoc202003058 Previous Articles Next Articles

高效镁催化的羧酸硼氢化反应

郑玉坤^a, 曹旭^a, 李佳^a, 华海明^a, 姚薇薇^b, 赵斌林^a, 马猛涛^a

a 南京林业大学理学院南京 210037;
b 南京中医药大学药学院南京 210023

收稿日期:2020-03-25 修回日期:2020-04-26 发布日期:2020-05-11
通讯作者: 姚薇薇, 赵斌林, 马猛涛 E-mail:yww0715@hotmail.com;zblchemistry@163.com;mengtao@njfu.edu.cn
基金资助:
国家自然科学基金（Nos.21772093，21372117）和江苏省自然科学基金（No.BK20181421）资助项目.

Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids

Zheng Yukun^a, Cao Xu^a, Li Jia^a, Hua Haiming^a, Yao Weiwei^b, Zhao Binlin^a, Ma Mengtao^a

a College of Science, Nanjing Forestry University, Nanjing 210037;
b College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023

Received:2020-03-25 Revised:2020-04-26 Published:2020-05-11
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772093, 21372117) and the Natural Science Foundation of Jiangsu Province (No. BK20181421).

1. 202086S.pdf(2780KB)

Abstract

Sterically bulky amino magnesium methyl complex, LMgCH₃(THF)₂ (L=NAr(SiMe₃), Ar=4,2,6-Me(CHPh₂)₂-C₆H₂) has been employed as an efficient precatalyst for the deoxygenate hydroboration of a variety of aromatic and aliphatic acids with pinacolborane (HBpin) under mild reaction condition. Additionally, chemoselective hydroboration of carboxylic acids over esters was also achieved under the standard conditions. Two plausible reaction mechanisms were proposed based on the density functional theory (DFT) calculations and stoichiometric reactions.

Key words: hydroboration, carboxylic acid, magnesium, main group metal

Cite this article

Zheng Yukun, Cao Xu, Li Jia, Hua Haiming, Yao Weiwei, Zhao Binlin, Ma Mengtao. Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2086-2093.

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高效镁催化的羧酸硼氢化反应

Efficient Magnesium-Catalyzed Hydroboration of Carboxylic Acids

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