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Ligand‐Enabled δ‐C(sp<sup>3</sup>)−H Borylation of Aliphatic Amines

Hediyala B. Chandrashekar, Pravas Dolui, Bijin Li, Astam Mandal, Hao Liu, Srimanta Guin, Haibo Ge, Debabrata Maiti

2021Angewandte Chemie International Edition37 citationsDOI

Abstract

Abstract Directed C−H functionalization has been realized as a complimentary technique to achieve borylation at a distal position of aliphatic amines. Here, we demonstrated the oxidative borylation at the distal δ‐position of aliphatic amines using various borylating agents, a palladium catalyst, and a rightly tuned ligand in the presence of a cheap oxidant. Moreover, an organopalladium δ‐C(sp 3 )‐H‐activated intermediate has been isolated and crystallographically characterized to get mechanistic insight.

Topics & Concepts

BorylationLigand (biochemistry)ChemistryStereochemistryBiochemistryOrganic chemistryReceptorArylAlkylCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistrySynthesis and Catalytic Reactions
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