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

Inorg Chem. 2023 Oct 16;62(41):16867-16873. doi: 10.1021/acs.inorgchem.3c02424. Epub 2023 Oct 4.

Authors

Yeow-Chuan Teo¹, Dexter Loh¹, Bi-Xiang Leong¹, Zheng-Feng Zhang², Ming-Der Su^{2

3}, Cheuk-Wai So¹

Affiliations

¹ School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371.
² Department of Applied Chemistry, National Chiayi University, Chiayi 60004, Taiwan.
³ Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.

PMID: 37792481
DOI: 10.1021/acs.inorgchem.3c02424

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.