Aluminum-Catalyzed Hydroboration of Alkenes

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Abstract

The aluminum-catalyzed hydroboration of alkenes with HBpin is reported using simple commercially available aluminum
hydride precatalysts [LiAlH4 or sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al)]. Good substrate scope and functional
group tolerance is demonstrated for alkene hydroboration, and the protocol was also applied to the hydroboration of ketone,
ester and nitrile functional groups, showing the potential for wider application. The aluminum-catalyzed hydroboration is proposed
to proceed by alkene hydroalumination which generates an alkyl aluminum species that undergoes s-bond metathesis with HBpin
to drive turnover of the catalytic cycle.
Original languageEnglish
Pages (from-to)2001-2005
JournalACS Catalysis
Volume8
Issue number3
Early online date29 Mar 2018
DOIs
Publication statusE-pub ahead of print - 29 Mar 2018

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