Heck-Type Coupling of Fused Bicyclic Vinylcyclopropanes: Synthesis of 1,2-Dihydropyridines, 2,3-Dihydro-1H-azepines, 1,4-Cyclohexadienes and 2H-Pyrans was written by Wurzer, Nikolai;Klimczak, Urszula;Babl, Tobias;Fischer, Sebastian;Angnes, Ricardo A.;Kreutzer, Dominik;Pattanaik, Aryaman;Rehbein, Julia;Reiser, Oliver. And the article was included in ACS Catalysis in 2021.Recommanded Product: tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate This article mentions the following:
Herein, a versatile approach for the endocyclic ring opening of bicyclic vinylcyclopropanes triggered by Heck arylations was reported. The key step for this transformation was a 闁?C-elimination allowing the ring expansion of cyclopropanated pyrroles, piperidines, furans, as well as cyclopentadienes to grant access to the corresponding 1,2-dihydropyridines such as I [R = 1-cyclohexenyl, Ph, 1-naphthyl, etc.], 2H-pyrans II [R1 = Ph, 4-MeOC6H4, 4-MeC6H4, etc.], 2,3-dihydro-1H-azepines III [R2 = 4-ClC6H4, Ph, etc.], and 1,4-cyclohexadienes IV [R3 = 4-i-PrC6H4, 2-naphthyl, etc.], resp. Addnl., gem-disubstituted cyclopropanated furans showed unexpected behavior by giving diastereoselectively asym. substituted dienes. Mechanistic studies and theor. calculations point toward a facile 闁?C-elimination with a concomitant shift of Pd along the cyclopropane moiety, which could be successfully compete with the usual termination step of a Heck reaction via a syn-闁?hydride elimination. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Recommanded Product: tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate).
tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine derivatives are also useful as small-molecule 婵?helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Recommanded Product: tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate