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Neosilyllithium‐Catalyzed Hydroboration of Alkynes and Alkenes in the Presence of Pinacolborane (HBpin)
Author(s) -
Kumar Gobbilla Sai,
Moorthy Shruti,
Karmakar Himadri,
Singh Saurabh Kumar,
Panda Tarun K.
Publication year - 2022
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202100895
Subject(s) - chemistry , hydroboration , reactivity (psychology) , alkyne , alkyl , intramolecular force , intermolecular force , catalysis , medicinal chemistry , organic chemistry , molecule , medicine , alternative medicine , pathology
We report here a novel protocol for the hydroboration of alkynes and alkenes, which in the presence of neosilyllithium (LiCH 2 SiMe 3 ) (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 LiCH 2 SiMe 3 ‐catalyzed alkyne hydroboration.