Neosilyllithium‐Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)

Kumar, Gobbilla Sai and Moorthy, Shruti and Karmakar, Himadri and Singh, Saurabh Kumar and Panda, Tarun K. (2022) Neosilyllithium‐Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin). European Journal of Inorganic Chemistry, 2022 (2). ISSN 1434-1948

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Abstract

We report here a novel protocol for the hydroboration of alkynes and alkenes, which in the presence of neosilyllithium (LiCH2SiMe3) (5 mol %) and pinacolborane efficiently results in the formation of corresponding alkenyl and alkyl boronate ester products in good yields. The electron-donating and electron-withdrawing substituents on the aromatic rings of alkynes and alkenes converted smoothly to the desired products. When we extended the scope of reactivity to various aliphatic alkynes and styrenes using similar conditions, the alkenyl and alkyl boronate ester products were again formed in good yields. We also performed intramolecular and intermolecular reactions to check the reactivity of different functional groups on the phenyl ring. Experimental investigations and DLPNO-CCSD(T) calculations reveal mechanistic insights from the LiCH2SiMe3-catalyzed alkyne hydroboration. © 2021 Wiley-VCH GmbH

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IITH Creators:

IITH Creators	ORCiD
Singh, Saurabh Kumar	UNSPECIFIED
Panda, Tarun K	http://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). G. S. K. thanks to the DST-Inspire Fellowship India (IF180108). H. K. thanks CSIR India, and S. M. thanks MoE and IIT Hyderabad for their 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:

neosilyllithium (LiCH2SiMe3) (5 mol %), pinacolborane, alkenyl and alkyl boronate ester products, aromatic rings of alkynes and alkenes.

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

14 Jul 2022 12:36

Last Modified:

14 Jul 2022 12:36