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钪催化烯烃与脂肪族叔胺的分子间氢胺烷基化反应。

Scandium-catalysed intermolecular hydroaminoalkylation of olefins with aliphatic tertiary amines.

作者信息

Nako Adi E, Oyamada Juzo, Nishiura Masayoshi, Hou Zhaomin

机构信息

Organometallic Chemistry Laboratory and RIKEN Center for Sustainable Resource Science , RIKEN , 2-1 Hirosawa, Wako , Saitama , 351-0198 , Japan . Email:

出版信息

Chem Sci. 2016 Oct 1;7(10):6429-6434. doi: 10.1039/c6sc02129h. Epub 2016 Jul 4.

DOI:10.1039/c6sc02129h
PMID:28451099
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5356020/
Abstract

A homoleptic scandium trialkyl complex in combination with a borate compound served as an excellent catalyst for the C-H addition of aliphatic tertiary amines to olefins. This highly regiospecific, 100% atom efficient C-H bond alkylation reaction was applicable to a wide variety of tertiary amines and olefins, including functionalised styrenes and unactivated α-olefins. This work represents the first example of rare-earth catalysed olefin hydroaminoalkylation and also the first example of catalytic C-H addition of aliphatic tertiary amines to olefins with any catalyst.

摘要

一种均配型三烷基钪配合物与一种硼酸盐化合物组合,可作为将脂肪族叔胺的C-H加成到烯烃上的优异催化剂。这种具有高度区域选择性、100%原子经济性的C-H键烷基化反应适用于多种叔胺和烯烃,包括官能化苯乙烯和未活化的α-烯烃。这项工作代表了稀土催化烯烃氢胺烷基化的首个实例,也是使用任何催化剂将脂肪族叔胺的C-H加成到烯烃上的首个实例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b33e/5356020/6ebbd55308bc/c6sc02129h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b33e/5356020/42201d5679c8/c6sc02129h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b33e/5356020/6ebbd55308bc/c6sc02129h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b33e/5356020/42201d5679c8/c6sc02129h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b33e/5356020/6ebbd55308bc/c6sc02129h-s2.jpg

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2
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J Am Chem Soc. 2016 May 18;138(19):6147-50. doi: 10.1021/jacs.6b03859. Epub 2016 May 10.
3
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