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Intermolecular Vicinal Diaminative Assembly of Tetrahydroquinoxalines via Metal-free Oxidative [4 + 2] Cycloaddition Strategy
journal contribution
posted on 2020-03-09, 04:29 authored by Dangui Wang, Huaibin Yu, Shaohan Sun, Fangrui ZhongReported herein is the first metal-free
oxidative [4 + 2] coupling
of o-phenylenediamines with various alkenes. Differing
from the known strategy that hinged on reactive π-allyl Pd intermediates
from restrained allylic alcohol/acetate and diene substrates, this
metal-free method features easy accessibility of starting materials,
step economy, benign reaction conditions, and more importantly broad
C–C double bonds (styrenes, vinyl (thio)ethers, benzofurans,
indoles) with diastereospecificities. Mechanistic studies suggest
the intermediacy of the benzoquinone diimides, a class of useful but
yet underexploited synthons. Of note, they efficiently furnished functionalized
tetrahydroquinoxalines and complement the well-studied alkene
vicinal diamination typically toward acyclic diamine derivatives.
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Keywords
reaction conditionsphenylenediaminebenzoquinone diimidesaccessibilitycomplementStrategyIntermolecular Vicinal Diaminative AssemblyMechanistic studiesTetrahydroallylicfunctionalizedDifferingintermediacystrategyReportedMetal-freemetal-free method featuresOxidativestep economyindolematerialtetrahydrobenzofurandiene substratesdiastereospecificitieoxidativewell-studied alkene vicinal diaminationacyclic diamine derivativesreactive π- allyl Pd intermediatesthiostyreneunderexploited synthonsCycloadditionbond
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