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Title: A NHC-silyliumylidene cation for catalytic N‑formylation of amines using carbon dioxide
Authors: Leong, Bi-Xiang
Teo, Yeow-Chuan
Condamines, Cloé
Yang, Ming-Chung
Su, Ming-Der
So, Cheuk-Wai
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2020
Source: Leong, B., Teo, Y., Condamines, C., Yang, M., Su, M. & So, C. (2020). A NHC-silyliumylidene cation for catalytic N‑formylation of amines using carbon dioxide. ACS Catalysis, 10(24), 14824-14833.
Journal: ACS Catalysis
Abstract: This study describes the use of a silicon(II) complex, namely, the NHC-silyliumylidene cation complex [(I ) SiH]I (1, I =:C{N(Me)C(Me)} ), to catalyze the chemoselective N-formylation of primary and secondary amines using CO and PhSiH under mild conditions to afford the corresponding formamides as a sole product (average reaction time: 4.5 h; primary amines, average yield: 95%, average TOF: 8 h ; secondary amines, average yield: 98%, average TOF: 17 h ). The activity of 1 and product yields outperform the currently available non-transition-metal catalysts used for this catalysis. Mechanistic studies show that the silicon(II) center in complex 1 catalyzes the C−N bond formation via a different pathway in comparison with non-transition-metal catalysts. It sequentially activates CO , PhSiH , and amines, which proceeds via a dihydrogen elimination mechanism, to form formamides, siloxanes, and dihydrogen gas.
ISSN: 2155-5435
DOI: 10.1021/acscatal.0c03795
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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