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- W4242816892 abstract "Herein, we report a versatile approach for the endocyclic ring-opening of bicyclic vinylcyclopropanes triggered by Heck arylations. Key step for this transformation is a [1,3]-migratory shift of Pd allowing the ring expansion of cyclopropanated pyrroles, piperidines, furans as well as cyclopentadienes to grant access to the corresponding 1,2-dihydropyridines, 2<i>H</i>-pyrans, 2,3-dihydro-1<i>H</i>-azepines and 1,4-cyclohexadienes, respectively. Additionally, <i>gem</i>-disubstituted cyclopropanated furans showed unexpected behavior by giving diastereoselectively asymmetrically substituted dienes. Mechanistic studies and theoretical calculations point towards a facile [1,3]-migratory shift of Pd along the cyclopropane moiety, which can successfully compete with the usual termination step of a Heck reaction via a <i>syn</i>-b-hydride elimination.<br>" @default.
- W4242816892 created "2022-05-12" @default.
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- W4242816892 date "2021-06-07" @default.
- W4242816892 modified "2023-10-18" @default.
- W4242816892 title "Heck-Type Coupling of Fused Bicyclic Vinylcyclopropanes: Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-1H-Azepines, 1,4-Cyclohexadienes, 2H-Pyrans, and 1,3-Butadienes" @default.
- W4242816892 doi "https://doi.org/10.26434/chemrxiv.14731455" @default.
- W4242816892 hasPublicationYear "2021" @default.
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