Abstract
AbstractThis study describes the use of an amidinato isopropylmethylamidosilylene [LSiN(Me)iPr] (1, L=PhC(NtBu)2) to catalyze hydroboration of carbonyl compounds. Compound 1 (loading: 5–10 mol%) was shown to be an efficient catalyst for the chemoselective hydroboration of aldehydes (average yield=97 %, average TOF=8.8 h−1) and ketones (average yield=97 %, average TOF=1.7 h−1) with pinacolborane (HBpin) in C6D6 at 90 °C to form borate esters. Mechanistic studies show that the Si lone pair electrons on 1 and the B vacant p orbital of HBpin activates the C=O double bond of aldehydes and ketones, the intermediates of which undergoes hydroboration to yield borate esters and regenerate compound 1.
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