2023
DOI: 10.1021/acscatal.3c00619
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Carbon-Centered Radical with Leaving Group-Mediated Ring Opening of Cyclopropenes via the Rearrangement of Cyclopropyl to the Allyl Radical: A General Access to Multisubstituted 1,3-Dienes

Abstract: We design and develop a general strategy for the assembly of multisubstituted 1,3-diene derivatives. This methodology proceeds through the cleavage of cyclopropenes via the rearrangement of the cyclopropyl radical to the allyl radical after the addition of a carbon-centered radical with a leaving group onto the strained double bond, leading to 1,3-diene products with the release of the leaving group. This approach represents a reaction mode for carbon-centered radical-mediated functionalization of cyclopropene… Show more

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Cited by 5 publications
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“…Over the past two decades, our group and others have developed a transition-metal-catalyzed MCR strategy involving electrophilic trapping of onium ylides generated from metal carbenes with nucleophiles, providing an ingenious difunctionalization strategy for diazo compounds to access structurally complex and diverse molecules ( Scheme 1b , top) [ 28 29 ]. In recent years, radical-mediated MCRs with diazo compounds have become a highly emerging area of research and exhibit complementary reactivity to those well-developed carbene-mediated MCRs [ 30 42 ]. In the radical-mediated difunctionalization of alkenes, the carbon-centered radical species from a diazo compound can add to diverse alkenes followed by a diradical coupling or radical addition process to achieve the difunctionalization ( Scheme 1b , middle) [ 32 37 ].…”
Section: Introductionmentioning
confidence: 99%
“…Over the past two decades, our group and others have developed a transition-metal-catalyzed MCR strategy involving electrophilic trapping of onium ylides generated from metal carbenes with nucleophiles, providing an ingenious difunctionalization strategy for diazo compounds to access structurally complex and diverse molecules ( Scheme 1b , top) [ 28 29 ]. In recent years, radical-mediated MCRs with diazo compounds have become a highly emerging area of research and exhibit complementary reactivity to those well-developed carbene-mediated MCRs [ 30 42 ]. In the radical-mediated difunctionalization of alkenes, the carbon-centered radical species from a diazo compound can add to diverse alkenes followed by a diradical coupling or radical addition process to achieve the difunctionalization ( Scheme 1b , middle) [ 32 37 ].…”
Section: Introductionmentioning
confidence: 99%