On the Viability of Carbonyl Hydroboration Catalysed by Aluminium Hydrides.

ABSTRACT: The hydroboration of aldehydes and ketones by pinacolborane (HBpin) catalysed by (Nacnac)^DippAl(OTf)H ((Nacnac)^Dipp = HC(MeCDippN)₂; Dipp = C₆H₃ ⁱPr₂-2,6; Tf = SO₂CF₃) was first reported in 2015. This study represented a landmark in main group catalysis, and advanced a widely-accepted and oft-cited mechanistic paradigm. However, in contradiction of that study, we show here that: i) the mechanism proposed, involving turnover via Al─O/B─H metathesis at the intermediate (Nacnac)^DippAl(OTf)(OCH₂Ph), does not occur; ii) when using pre-purified HBpin, the hydroboration reaction with acetophenone 'catalysed' by (Nacnac)^DippAl(OTf)H (reportedly giving 51% conversion o

SUBMITTER: Caise A 

PROVIDER: S-EPMC12603974 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature