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钴催化的高效贝克曼重排反应

姚武冰 虞姜姜 黄相韵 张斌

高等学校化学学报2018,Vol.39Issue(5):926-933,8.
高等学校化学学报2018,Vol.39Issue(5):926-933,8.DOI:10.7503/cjcu20170560

钴催化的高效贝克曼重排反应

A Highly Efficient Co-catalytic Beckmann Rearrangement Reaction

姚武冰 1虞姜姜 1黄相韵 1张斌1

作者信息

  • 1. 台州学院医药化工学院,台州318000
  • 折叠

摘要

Abstract

Beckmann rearrangement reaction represents one of the most significant reactions in organic synthe-sis,and plays a very important role in the field of synthetic chemistry.The traditional Beckmann rearrangement reactions generally require high temperature and strong acids,and suffer from harsh conditions and serious en-vironmental pollution. In this work, based on the efficient and commercial available cobalt tetrafluoroborate hexahydrate,the catalyst systems capable of highly efficient catalytic Beckmann rearrangement of ketoxime de-rivatives were developed,providing the amides with broad functional-group compatibility and high yields(up to 97%). With the active Co-catalyst in hands,the catalytic system also successfully conducted the transforman-tion on a 10 gram-grade scale,gaving the desirable product in 71% yield. Moreover, the Co-catalyzed Beck-mann rearrangement reaction was extended to a one-pot protocol using ketone and hydroxylamine hydrochloride as reactive materials,offering the yield of products up to 94%. The novel system proceeded with additives and solvent free,and showed high atom-economy and good functional-group tolerance.

关键词

贝克曼重排/钴催化剂//酮肟/酰胺

Key words

Beckmann rearrangement/Cobalt catalyst/Ketone/Ketoxime/Amide

分类

化学化工

引用本文复制引用

姚武冰,虞姜姜,黄相韵,张斌..钴催化的高效贝克曼重排反应[J].高等学校化学学报,2018,39(5):926-933,8.

基金项目

国家级大学生创新创业训练计划项目(批准号:201710350018)资助. Supported by the National Undergraduate Training Programs for Innovation and Entrepreneurship, China(No.201710350018). (批准号:201710350018)

高等学校化学学报

OA北大核心CSCDCSTPCD

0251-0790

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