NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane

Yeow Chuan Teo; Dexter Loh; Bi Xiang Leong; Zheng Feng Zhang; Ming Der Su; Cheuk Wai So

doi:10.1021/acs.inorgchem.3c02424

NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane

Yeow Chuan Teo, Dexter Loh, Bi Xiang Leong, Zheng Feng Zhang, Ming Der Su^*, Cheuk Wai So^*

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The low-oxidation-state silicon-catalyzed hydroboration of isocyanates with pinacolborane (HBpin) using the NHC-silyliumylidene cation catalyst [(IMe)₂SiH]I (1, IMe = :C{N(Me)C(Me)}₂) is described. In the catalysis, the Si lone pair electrons activate isocyanates, and the latter react with HBpin to form N-boryl formamides at room temperature. Catalyst 1 further activates N-boryl formamides at 70 °C, the intermediates of which react with HBpin to form N-boryl methylamines and (pinB)₂O.

Original language	English
Pages (from-to)	16867-16873
Number of pages	7
Journal	Inorganic Chemistry
Volume	62
Issue number	41
DOIs	https://doi.org/10.1021/acs.inorgchem.3c02424
Publication status	Published - Oct 16 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/acs.inorgchem.3c02424

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title = "NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane",

abstract = "The low-oxidation-state silicon-catalyzed hydroboration of isocyanates with pinacolborane (HBpin) using the NHC-silyliumylidene cation catalyst [(IMe)2SiH]I (1, IMe = :C{N(Me)C(Me)}2) is described. In the catalysis, the Si lone pair electrons activate isocyanates, and the latter react with HBpin to form N-boryl formamides at room temperature. Catalyst 1 further activates N-boryl formamides at 70 °C, the intermediates of which react with HBpin to form N-boryl methylamines and (pinB)2O.",

author = "Teo, {Yeow Chuan} and Dexter Loh and Leong, {Bi Xiang} and Zhang, {Zheng Feng} and Su, {Ming Der} and So, {Cheuk Wai}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

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doi = "10.1021/acs.inorgchem.3c02424",

language = "English",

volume = "62",

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journal = "Inorganic Chemistry",

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TY - JOUR

T1 - NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane

AU - Teo, Yeow Chuan

AU - Loh, Dexter

AU - Leong, Bi Xiang

AU - Zhang, Zheng Feng

AU - Su, Ming Der

AU - So, Cheuk Wai

PY - 2023/10/16

Y1 - 2023/10/16

N2 - The low-oxidation-state silicon-catalyzed hydroboration of isocyanates with pinacolborane (HBpin) using the NHC-silyliumylidene cation catalyst [(IMe)2SiH]I (1, IMe = :C{N(Me)C(Me)}2) is described. In the catalysis, the Si lone pair electrons activate isocyanates, and the latter react with HBpin to form N-boryl formamides at room temperature. Catalyst 1 further activates N-boryl formamides at 70 °C, the intermediates of which react with HBpin to form N-boryl methylamines and (pinB)2O.

AB - The low-oxidation-state silicon-catalyzed hydroboration of isocyanates with pinacolborane (HBpin) using the NHC-silyliumylidene cation catalyst [(IMe)2SiH]I (1, IMe = :C{N(Me)C(Me)}2) is described. In the catalysis, the Si lone pair electrons activate isocyanates, and the latter react with HBpin to form N-boryl formamides at room temperature. Catalyst 1 further activates N-boryl formamides at 70 °C, the intermediates of which react with HBpin to form N-boryl methylamines and (pinB)2O.

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DO - 10.1021/acs.inorgchem.3c02424

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JO - Inorganic Chemistry

JF - Inorganic Chemistry

IS - 41

ER -

NHC-Silyliumylidene Cation-Catalyzed Hydroboration of Isocyanates with Pinacolborane

Abstract

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