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

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.

SUBMITTER: Sapsford JS

PROVIDER: S-EPMC5901005 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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

Sapsford Joshua S JS Scott Daniel J DJ Allcock Nathan J NJ Fuchter Matthew J MJ Tighe Christopher J CJ Ashley Andrew E AE

Advanced synthesis & catalysis 20180115 6

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 si ...[more]

PMID: 29706853

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