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Direct synthesis of branched amines enabled by dual-catalyzed allylic C─H amination of alkenes with amines

Yufeng Ren, Bi-Hong Chen, Xiaoyi Chen, Hai‐Wu Du, Yulong Li, Wei Shu

2024Science Advances20 citationsDOIOpen Access PDF

Abstract

Direct conversion of hydrocarbons into amines represents an important and atom-economic goal in chemistry for decades. However, intermolecular cross-coupling of terminal alkenes with amines to form branched amines remains extremely challenging. Here, a visible-light and Co-dual catalyzed direct allylic C─H amination of alkenes with free amines to afford branched amines has been developed. Notably, challenging aliphatic amines with strong coordinating effect can be directly used as C─N coupling partner to couple with allylic C─H bond to form advanced amines with molecular complexity. Moreover, the reaction proceeds with exclusive regio- and chemoselectivity at more steric hinder position to deliver primary, secondary, and tertiary aliphatic amines with diverse substitution patterns that are difficult to access otherwise.

Topics & Concepts

Allylic rearrangementAminationChemoselectivityChemistrySteric effectsCatalysisIntermolecular forceCombinatorial chemistryPrimary (astronomy)Atom economyDual roleOrganic chemistryMoleculeAstronomyPhysicsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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