Asymmetric β-arylation of cyclopropanols enabled by photoredox and nickel dual catalysis

Abstract

The enantioselective functionalization and transformation of readily available cyclopropyl compounds are synthetically appealing yet challenging topics in organic synthesis. Here we report an asymmetric β-arylation of cyclopropanols with aryl bromides...

Catalytic asymmetric intramolecular propargylation of cyclopropanols to access the cuparane core

“…[15][16][17][18][19][20][21][22] These studies together with our experience [25][26][27][28][29][30] and others' reports [31][32][33][34][35][36] on ring-opening reactions of cyclopropanols indicate that how to activate the cyclopropanol unit is key to the success of the ring-opening reactions of cyclopropanols and thus should be identied primarily. Furthermore, an asymmetric catalytic system applicable to the reaction of cyclopropanol remains underdeveloped, [9][10][11][12][13][14][37][38][39][40][41][42][43] which highlights the need to establish an effective asymmetric catalytic system for this new reaction.…”

Ring‐Opening Coupling Reaction of Cyclopropanols with Electrophilic Alkenes Enabled by Decatungstate as Photoredox Catalyst

“…[5,6,10,11,14] Currently, photoredox catalysis offers a number of bypassing strategies that allow the generation of ketoalkyl radicals from cyclopropanols [15,16] and even unstrained cycloalkanols under mild conditions. [17] This process can readily occur through proton-coupled electron transfer (PCET), [17][18][19][20][21][22][23][24] photoinduced ligand-tometal charge transfer, [25][26][27][28][29] or by photocatalytic single electron transfer (SET) oxidation, which typically requires stoichiometric oxidants. [15,30,31] There are some reported examples of photocatalytic ring-opening coupling reactions of cyclopropanols with electrophilic alkenes.…”

Ring-Opening Cross-Coupling of Cyclopropanols with Electrophilic Alkenes via Photoinduced Charge Transfer Facilitated by Decatungstate Catalyst

“…Similarly to the previous works, [18,19] we expected that the produced radicals B could be intercepted by electron-deficient alkenes 2 to furnish a new C-C bond in the respective adducts 3. Although β-ketoalkyl radical-mediated transformations are widespread in the chemistry of cyclopropanols, [26,27] not much attention has been paid to generate these species in a photocatalytic manner, [23,[28][29][30][31][32][33][34] and especially to enable their reactions with electron-deficient alkenes. The group of Yamamoto used proton-coupled electron transfer (PCET) strategy for the intramolecular reaction of cyclopropanols and electron-deficient alkenes leading to the ring expansion.…”