Hydroboration of nitriles, esters, and amides catalyzed by simple neosilyllithium

Sai Kumar, G. and Kumar, S S and Panda, Tarun K and et al, . (2022) Hydroboration of nitriles, esters, and amides catalyzed by simple neosilyllithium. Polyhedron, 219. pp. 1-9. ISSN 0277-5387

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We present here an efficient method for the hydroboration of organic nitriles, carboxylic esters, and carboxamides with pinacolborane (HBpin) using an alkali metal catalyst, neosilyllithium (LiCH2SiMe3), in neat reaction conditions. The reactions were accomplished with efficient catalytic reactivity and demonstrated by neosilyllithium at room temperature, in solvent-free condition, to afford a high yield of the corresponding N-boryl amines, boryl ethers, and amine hydrochlorides. The protocol for the catalytic reaction presented in this paper is simple and efficient, with diverse substrate scope for nitriles, carboxylic esters, and carboxamides showing excellent functional group tolerance. DLPNO-CCSD(T) calculations were also performed, showing that the hydroboration of nitriles catalyzed by neosilyllithium occurs through the pre-coordination of the nitrile at Lewis acid lithium followed by hydride migration from the B–H entity. © 2022 Elsevier Ltd

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IITH Creators:
IITH CreatorsORCiD
Panda, Tarun Khttp://orcid.org/0000-0003-0975-0118
Item Type: Article
Additional Information: This work is financially supported by the Indian Institute of Technology Hyderabad (IITH). S. K. S. thanks IIT Hyderabad and the Department of Science and Technology for the Start-up Research Grant (SRG/2020/001323). A. B. acknowledged the higher education department of Govt of West Bengal. Equal contribution from the authors G. S. K. and J. B. G. S. K. thanks to the DST-Inspire Fellowship India (IF180108). S. M. thanks The Prime Minister’s Research Fellows (PMRF) Scheme for her Ph.D. fellowship. The support and resources provided by PARAM Shivay Facility under the National Supercomputing Mission, Government of India at the Indian Institute of Technology, Varanasi, are gratefully acknowledged.
Uncontrolled Keywords: Carboxamides, Carboxylic esters, Hydroboration, Neosilyllithium, Nitriles, Pinacolborane
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: . LibTrainee 2021
Date Deposited: 25 Jun 2022 04:57
Last Modified: 27 Jun 2022 04:15
URI: http://raiith.iith.ac.in/id/eprint/9388
Publisher URL: https://doi.org/10.1016/j.poly.2022.115784
OA policy: https://v2.sherpa.ac.uk/id/publication/4678
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