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Rapid access to <i>t</i>-butylalkylated olefins enabled by Ni-catalyzed intermolecular regio- and <i>trans</i>-selective cross-electrophile <i>t</i>-butylalkylation of alkynes

Yizhou Zhan, Huan Meng, Wei Shu

2022Chemical Science27 citationsDOIOpen Access PDF

Abstract

-selective cross-dialkylation of alkynes with two distinct alkyl bromides to afford olefins with two aliphatic substituents. The reductive conditions circumvent the use of organometallic reagents, enabling the cross-dialkylation process to occur at room temperature from two different alkyl bromides. This operationally simple protocol provides a straightforward and practical access to a wide range of stereodefined dialkylated olefins with broad functional group tolerance from easily available starting materials.

Topics & Concepts

ChemistryAlkylElectrophileReagentStereoselectivityCatalysisReductive eliminationCombinatorial chemistryIntermolecular forceMedicinal chemistryOrganic chemistryMoleculeCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions