转自：康龙化成

ElectrochemicalCyanationofAlcoholsEnabledbyanIodide-MediatedPhosphineP(V/III)RedoxCouple

XuewenGuo,NathanG.Price,andQileiZhu*

DepartmentofChemistry,UniversityofUtah,SaltLakeCity,Utah84112,UnitedStates

—Org.Lett.,2024,DOI:10.1021/acs.orglett.4c02550

RecommendedbyChaoyouLiu_PDM

Keywords:Cyanation(反应类型),electrochemistry(反应类型),C(sp3)-C(sp)(成键类型),alcohol(原料),cyanohydrin(试剂),alkylnitriles(产物)

ABSTRACT:Authorsreporthereinamildelectrochemicalmethodtotransformalcoholsintotheircorrespondingnitrilesbyusingcommerciallyavailablereagents.Thisprotocolacceptssubstrateswithvariousfunctionalgroupsincludingthosethataresusceptibletooxidativedecomposition.Mechanisticstudiesrevealedacriticaliodide-mediatedphosphineelectrochemicaloxidationpathwayleadingtothealkoxyphosphoniumintermediate,followedbynucleophilicsubstitutionbyacyanidenucleophile.Thismethoddemonstratestheuseofelectrochemistryinreplacingazo-typereagentsindirectnucleophilicsubstitutionandhomologationofalcoholsubstrates.

Background

OptimizationofReactionConditions

SubstrateScope

ProposedReactionMechanism

（转自：康龙化成）

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