Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid

Joshua Sapsford; Daniel Scott; Nathan Allcock; Matthew J. Fuchter; Christopher Tighe; Andrew Ashley

doi:10.1002/adsc.201701418

Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid

Joshua Sapsford, Daniel Scott, Nathan Allcock, Matthew J. Fuchter, Christopher Tighe, Andrew Ashley

Department of Chemistry

Imperial College London

Research output: Contribution to journal › Article › peer-review

41 Citations (SciVal)

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.

Original language	English
Pages (from-to)	1066-1071
Journal	Advanced Synthesis & Catalysis
Volume	360
Issue number	6
DOIs	https://doi.org/10.1002/adsc.201701418
Publication status	Published - 20 Mar 2018

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abstract = "Despite the ever-broadening applications of main-group {\textquoteleft}frustrated Lewis pair{\textquoteright} (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.",

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AU - Tighe, Christopher

AU - Ashley, Andrew

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AB - 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.

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DO - 10.1002/adsc.201701418

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IS - 6

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Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid

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