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https://hdl.handle.net/10356/149731
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. https://dx.doi.org/10.1021/acscatal.0c03795 | 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. | URI: | https://hdl.handle.net/10356/149731 | ISSN: | 2155-5435 | DOI: | 10.1021/acscatal.0c03795 | Schools: | School of Physical and Mathematical Sciences | 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 https://doi.org/10.1021/acscatal.0c03795 | Fulltext Permission: | open | Fulltext Availability: | With Fulltext |
Appears in Collections: | SPMS Journal Articles |
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A NHC-silyliumylidene cation for catalytic N‑formylation of amines using carbon dioxide.pdf | 1.61 MB | Adobe PDF | View/Open |
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