Frustrated Lewis Pair Chemistry of Chiral (+)-Camphor-Based Aminoboranes

被引：17

作者：

Lindqvist, Markus ^{[1
]}

Axenov, Kirill ^{[1
]}

Nieger, Martin ^{[1
]}

Raisanen, Minna ^{[1
]}

Leskela, Markku ^{[1
]}

Repo, Timo ^{[1
]}

机构：

[1] Univ Helsinki, Dept Chem, Inorgan Chem Lab, FIN-00014 Helsinki, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 31期

基金：

芬兰科学院;

关键词：

boron; frustrated Lewis pairs; hydrogenation; nitrogen; reaction mechanism; HETEROLYTIC DIHYDROGEN ACTIVATION; FREE CATALYTIC-HYDROGENATION; CORRESPONDING ALKENES; CONVENIENT CONVERSION; HYDROBORATION; ACID; REACTIVITY; ALDEHYDES; ENAMINES; KETONES;

D O I：

10.1002/chem.201300462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dimethylamino-(+)-camphorenamine reacted with an equimolar amount of Piers' borane, HB(C6F5)(2), to give the corresponding iminium-hydroborate zwitterionic salt. Being in equilibrium with the parent enamine-HB(C6F5)(2) N-B pair, this salt was able to split hydrogen heterolytically, hydrogenating the iminium group in the molecule. Detailed studies revealed that the hydrogen splitting in this reaction proceeded through an intermolecular pathway leading to a bornylamine-HB(C6F5)(2) adduct. When the starting enamine is present in excess over HB(C6F5)(2), the produced bornylamine-HB(C6F5)(2) adduct breaks up, eliminating free bornylamine and forming the initial camphorenamine- HB(C6F5)(2) pair. This results in hydrogenation of the camphorenamine framework in a catalytic fashion.

引用

页码：10412 / 10418

页数：7

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