Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1462-1471.DOI: 10.6023/cjoc202208042 Previous Articles     Next Articles

ARTICLES

氯化镁催化醛、酮及亚胺的化学选择性还原

张苗苗, 陈荣, 焦红梅, 马豪杰, 韩波*(), 张玉琦, 王记江   

  1. 延安大学化学与化工学院 新能源新功能材料重点实验室 陕西省化学反应工程重点实验室 陕西延安 716000
  • 收稿日期:2022-08-30 修回日期:2022-10-18 发布日期:2022-12-07
  • 通讯作者: 韩波
  • 作者简介:
    共同第一作者.
  • 基金资助:
    国家自然科学基金(22061041); 陕西省科技资源开放共享平台(2021PT-004); 延安大学博士科研启动经费(YDBK2019-60); 延安大学科研项目(YDY2020-61); 陕西省大学生创新创业训练计划(S202210719055)

MgCl2-Catalyzed Chemoselective Reduction of Aldehydes, Ketones and Imines

Miaomiao Zhang, Rong Chen, Hongmei Jiao, Haojie Ma, Bo Han(), Yuqi Zhang, Jijiang Wang   

  1. Laboratory of New Energy & New Function Materials, Shaanxi Key Laboratory of Chemical and Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000
  • Received:2022-08-30 Revised:2022-10-18 Published:2022-12-07
  • Contact: Bo Han
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22061041); Open Sharing Platform for Scientific and Technological Resources of Shaanxi Province(2021PT-004); Doctoral Research Foundation of Yan'an University(YDBK2019-60); Research Program of Yan'an University(YDY2020-61); Shaanxi Province Training Program of Innovation and Entrepreneurship for Undergraduates(S202210719055)

An operationally convenient Mg-catalyzed synthesis of alcohols by the reduction of aldehydes, ketones and α,β-unsaturated aldehydes/ketones is reported. It is a rare example of using mild and sustainable HBpin as a reductant for catalytic reduction of carbonyl compounds in the absence of acid or base as hydrolysis reagent. The reaction is up-scalable, and proceeds in high selectivity without the formation of boronate ester by-products, and tolerates sensitive functionalities such as iodine, bromide, chloride, fluoride, nitro, trifluoromethyl, aminomethyl, alkynyl, and amide. The MgCl2/HBpin combination has been also proved to be chemoselective for the C=N reduction of imine analogs.

Key words: alkaline-earth metals, magnesium, carbonyl, imine, reduction