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Lewis acid catalysis: regioselective hydroboration of alkynes and alkenes promoted by scandium triflate

Author:
Mandal, Souvik, Verma, Piyush Kumar, Geetharani, K.
Source:
Chemical communications 2018 v.54 no.97 pp. 13690-13693
ISSN:
1364-548X
Subject:
Lewis acids, alkenes, alkynes, catalytic activity, chemical reactions, regioselectivity, scandium
Abstract:
The first commercially available scandium-catalysed selective hydroboration of alkynes and alkenes with HBpin (pin = OC-Me₂CMe₂O) in the presence of a catalytic amount of NaHBEt₃ has been developed. This protocol can be applicable to a wide range of substrates including aromatic, aliphatic with cyclic and acyclic side chains, and heteroaryl systems with broad functional-group compatibility. Mechanistic studies revealed that the reaction occurs in a syn fashion via the σ-bond metathesis between the alkenyl scandium species and HBpin.
Agid:
6246702