Ni(bpy)(cod): A Convenient Entryway into the Efficient Hydroboration of Ketones, Aldehydes, and Imines

Abstract

The catalytic hydroboration of ketones, aldehydes, and imines with pinacol borane and Ni(bpy)(cod) has been demonstrated in benzene at room temperature and low catalyst loadings (0.03–0.3 mol-%). Spectroscopic and structural evidence support the formulation of Ni(bpy)(cod) as containing a Ni^I cation and a bpy^·– ligand. The Ni(bpy)(cod) complex reacts quickly with ketonic substrates to form an adduct that appears to function as an entryway into catalytic activity.

Innocent behavior? Ni(bpy)(cod) is an efficient precatalyst for the hydroboration of ketones, aldehydes, and imines. While the pre-catalyst contains a reduced bpy fragment, the catalytically active species does not. Mechanistic investigations suggest an entryway into the catalytic cycle that differs from generally accepted mechanisms of ketone hydroboration.

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