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 %, aver...

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Bibliographic Details
Published in:European journal of inorganic chemistry 2022-07, Vol.2022 (19), p.n/a
Main Authors: Lee, Jiawen, Fan, Jun, Koh, An‐Ping, Joslyn Cheang, Wan‐Jun, Yang, Ming‐Chung, Su, Ming‐Der, So, Cheuk‐Wai
Format: Article
Language:English
Subjects:
Aldehydes
Carbene homologues
Carbonyl compounds
Carbonyl ligands
Carbonyls
Esters
Hydroboration
Inorganic chemistry
Ketones
Silicon
Silylene
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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 °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. The amidinato isopropylmethylamidosilylene [LSiN(Me)iPr] (L=PhC(NtBu)2) is shown to be an efficient catalyst for the chemoselective hydroboration of aldehydes and ketones with pinacolborane to form borate esters. Mechanistic studies were carried out to determine the active catalyst and the reaction mechanism.
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.202200129