Direct reductive amination of carbonyl compounds catalyzed by a moisture tolerant Tin (IV) Lewis acid
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
Despite the ever-broadening applications of main-group ‘frustrated Lewis pair’ (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (>100 °C), represents a key barrier to their mainstream adoption. Herein we report that FLPs based on the Lewis acid iPr3SnOTf are moisture tolerant in the presence of moderately strong nitrogenous bases, even under high temperature regimes, allowing them to operate as simple and effective catalysts for the reductive amination of organic carbonyls, including for challenging bulky amine and carbonyl substrate partners.
Date Issued
2018-03-20
Date Acceptance
2017-12-15
Citation
Advanced Synthesis and Catalysis, 2018, 360 (6), pp.1066-1071
ISSN
1615-4150
Publisher
Wiley
Start Page
1066
End Page
1071
Journal / Book Title
Advanced Synthesis and Catalysis
Volume
360
Issue
6
Copyright Statement
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
License URL
Sponsor
The Royal Society
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (EPSRC)
The Royal Society
Grant Number
UF110061
EP/K030760/1
EP/N026004/1
n/a
UF160395
Subjects
Science & Technology
Physical Sciences
Chemistry, Applied
Chemistry, Organic
Chemistry
"frustrated Lewis pairs'
catalytic hydrogenation
water tolerance
reductive amination
tin
PAIR HYDROGENATION
FACILE PROTOCOL
KETONES
ALDEHYDES
ACTIVATION
AMINES
B(C6F5)(3)
DIHYDROGEN
CHEMISTRY
NITRILES
0305 Organic Chemistry
0904 Chemical Engineering
0302 Inorganic Chemistry
Organic Chemistry
Publication Status
Published
Date Publish Online
2017-12-28