A General C(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids
Rohan R. Merchant, Jovan A. Lopez
Abstract
A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl–alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.
Topics & Concepts
ChemistryAlkylSteric effectsReagentOrganic chemistryCombinatorial chemistrySubstrate (aquarium)Coupling reactionPrimary (astronomy)CatalysisOceanographyPhysicsGeologyAstronomyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions