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2023 , Vol. 43 >Issue 4: 1462 - 1471

DOI: https://doi.org/10.6023/cjoc202208042

研究论文

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
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  • 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
†共同第一作者.

收稿日期: 2022-08-30

  修回日期: 2022-10-18

  网络出版日期: 2022-12-12

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)

收起

MgCl2-Catalyzed Chemoselective Reduction of Aldehydes, Ketones and Imines

  • Miaomiao Zhang ,
  • Rong Chen ,
  • Hongmei Jiao ,
  • Haojie Ma ,
  • Bo Han ,
  • Yuqi Zhang ,
  • Jijiang Wang
Expand
  • 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
†These authors contributed equally to this work.
* Corresponding author.

Received date: 2022-08-30

  Revised date: 2022-10-18

  Online published: 2022-12-12

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)

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摘要

发展了一种操作简便、廉价实用的镁催化体系, 用于醛、酮及α,β-不饱和醛/酮的选择性还原, 制备了一系列醇类化合物. 以温和的HBpin为还原剂, 在没有酸或碱作为水解试剂的前提下, 高选择性地还原羰基, 体系中没有检测到硼酸酯副产物. 对碘、溴、氯、氟、硝基、三氟甲基、氨甲基、炔基和酰胺等官能团具有良好的兼容性, 在温和的条件下, MgCl2/HBpin催化体系不仅对羰基具有较高的催化活性, 对亚胺类底物具有高效的催化效果.

关键词： 碱土金属; 镁; 羰基; 亚胺; 还原

本文引用格式

张苗苗 , 陈荣 , 焦红梅 , 马豪杰 , 韩波 , 张玉琦 , 王记江 . 氯化镁催化醛、酮及亚胺的化学选择性还原[J]. 有机化学, 2023 , 43(4) : 1462 -1471 . DOI: 10.6023/cjoc202208042

Abstract

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

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