Expanding Water/Base Tolerant Frustrated Lewis Pair Chemistry to Alkylamines Enables Broad Scope Reductive Aminations.

ABSTRACT: Lower Lewis acidity boranes demonstrate greater tolerance to combinations of water/strong Brønsted bases than B(C₆ F₅ )₃ , this enables Si-H bond activation by a frustrated Lewis pair (FLP) mechanism to proceed in the presence of H₂ O/alkylamines. Specifically, BPh₃ has improved water tolerance in the presence of alkylamines as the Brønsted acidic adduct H₂ O-BPh₃ does not undergo irreversible deprotonation with aliphatic amines in contrast to H₂ O-B(C₆ F₅ )₃ . Therefore BPh₃ is a catalyst for the reductive amination of aldehydes and ketones with alkylamines using silanes as reductants. A range of amines inaccessible using B(C₆ F₅ )₃

SUBMITTER: Fasano V 

PROVIDER: S-EPMC5396349 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature