Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage

Patnaik, Smita; Sadow, Aaron D.

doi:10.1002/ange.201813305

Title: Interconverting Lanthanum Hydride and Borohydride Catalysts for C=O Reduction and C−O Bond Cleavage

Journal Article · 24 January 2019 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.201813305 · OSTI ID:1492099

Patnaik, Smita ^[1];

^[1]

Department of Chemistry and US Department of Energy Ames Laboratory Iowa State University 1605 Gilman Hall Ames IA USA

Abstract The high catalytic reactivity of homoleptic tris(alkyl) lanthanum La{C(SiHMe ₂ ) ₃ } ₃ is highlighted by C−O bond cleavage in the hydroboration of esters and epoxides at room temperature. The catalytic hydroboration tolerates functionality typically susceptible to insertion, reduction, or cleavage reactions. Turnover numbers (TON) up to 10 000 are observed for aliphatic esters. Lanthanum hydrides, generated by reactions with pinacolborane, are competent for reduction of ketones but are inert toward esters. Instead, catalytic reduction of esters requires activation of the lanthanum hydride by pinacolborane.

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Sponsoring Organization:: USDOE

OSTI ID:: 1492099

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 8 Vol. 131; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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