Amidinato Isopropylmethylamidosilylene-Catalyzed Hydroboration of Carbonyl Compounds

Jiawen Lee; Jun Fan; An Ping Koh; Wan Jun Joslyn Cheang; Ming Chung Yang; Ming Der Su; Cheuk Wai So

doi:10.1002/ejic.202200129

Amidinato Isopropylmethylamidosilylene-Catalyzed Hydroboration of Carbonyl Compounds

Jiawen Lee, Jun Fan, An Ping Koh, Wan Jun Joslyn Cheang, Ming Chung Yang, Ming Der Su^*, Cheuk Wai So^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

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.

Original language	English
Article number	e202200129
Journal	European Journal of Inorganic Chemistry
Volume	2022
Issue number	19
DOIs	https://doi.org/10.1002/ejic.202200129
Publication status	Published - Jul 8 2022
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

ASJC Scopus Subject Areas

Inorganic Chemistry

Keywords

Carbene homologues
Carbonyl ligands
Hydroboration
Silicon
Silylene

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title = "Amidinato Isopropylmethylamidosilylene-Catalyzed Hydroboration of Carbonyl Compounds",

abstract = "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.",

keywords = "Carbene homologues, Carbonyl ligands, Hydroboration, Silicon, Silylene",

author = "Jiawen Lee and Jun Fan and Koh, {An Ping} and {Joslyn Cheang}, {Wan Jun} and Yang, {Ming Chung} and Su, {Ming Der} and So, {Cheuk Wai}",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

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doi = "10.1002/ejic.202200129",

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volume = "2022",

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T1 - Amidinato Isopropylmethylamidosilylene-Catalyzed Hydroboration of Carbonyl Compounds

AU - Lee, Jiawen

AU - Fan, Jun

AU - Koh, An Ping

AU - Joslyn Cheang, Wan Jun

AU - Yang, Ming Chung

AU - Su, Ming Der

AU - So, Cheuk Wai

PY - 2022/7/8

Y1 - 2022/7/8

N2 - 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.

AB - 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.

KW - Carbene homologues

KW - Carbonyl ligands

KW - Hydroboration

KW - Silicon

KW - Silylene

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DO - 10.1002/ejic.202200129

M3 - Article

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SN - 1434-1948

VL - 2022

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 19

M1 - e202200129

ER -

Amidinato Isopropylmethylamidosilylene-Catalyzed Hydroboration of Carbonyl Compounds

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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