4.8 Article

Zinc-Catalyzed Hydrosilylation and Hydroboration of N-Heterocycles

Journal

ACS CATALYSIS
Volume 7, Issue 12, Pages 8454-8459

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02811

Keywords

zinc; hydrosilylation; hydroboration; N-heterocycles; DFT calculations

Funding

  1. American Chemical Society [53349-ND3]
  2. NSERC [2014-04410]

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The zinc hydride NacNacZnH (2) (NacNac = [Ar'NC(Me)CHC(Me)NAr'](-), Ar' = 2,6-Me2C6H3) catalyzes regioselective hydrosilylation and hydroboration of pyridines, including the hydroboration of phenanthroline. Mechanistic studies of hydrosilylation, including labeling, kinetic analysis, and density functional theory calculations, suggest the possibility of a reaction pathway based on hydride transfer from an out-of-sphere activated silane.

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