Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B–O Transborylation

Kieran Nicholson, Thomas Langer, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

Abstract

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B–O/B–H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B–O/B–H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B–O/B–H transborylation as key steps.
Original languageEnglish
Pages (from-to)2498-2504
JournalOrganic letters
Volume23
Issue number7
Early online date16 Mar 2021
DOIs
Publication statusE-pub ahead of print - 16 Mar 2021

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