Amidinato Isopropylmethylamidosilylene-catalyzed hydroboration of carbonyl compounds

Amidinato Isopropylmethylamidosilylene-catalyzed hydroboration of carbonyl compounds

This 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 %...

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Bibliographic Details
Main Authors: Lee, Jiawen, Fan, Jun, Koh, An-Ping, Cheang, Joslyn Wan-Jun, Yang, Ming-Chung, Su, Ming-Der, So, Cheuk-Wai
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Carbene Homologues
Carbonyl Ligands
Online Access:https://hdl.handle.net/10356/163350
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Institution: Nanyang Technological University
Language: English
Description
Summary:This 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 oC to form borate esters. Mechanistic studies shows 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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