Photoredox/nickel dual-catalyzed regioselective alkylation of propargylic carbonates for trisubstituted allenes

Abstract

Herein, a highly regioselective alkylation of propargylic carbonates for trisubstituted allenes with alkyl 1,4-dihydropyridines derivatives is developed via photoredox/ nickel dual-catalyzed process, which represents the first direct approach to access...

Radical transformations for allene synthesis

“…. 47 This highly regioselective method had good substrate scope and mild conditions. The study was initiated with the optimization of nickel catalysts, ligand, photocatalysts, and solvents.…”

“…In 2021, Liang et al disclosed a photoredox/nickel dual-catalyzed alkylation of propargylic carbonates with bench-stable alkyl 1,4-dihydropyridine derivatives (1,4-DHPs) as the alkyl radical precursors ( Scheme 24 ). 47 This highly regioselective method had good substrate scope and mild conditions. The study was initiated with the optimization of nickel catalysts, ligand, photocatalysts, and solvents.…”

Direct and efficient synthesis of tetrasubstituted allenyl organothiophosphates from propargylic alcohols under catalyst- and additive-free conditions

“…3 Commonly, these approaches for synthesizing allenes mainly include prototropic rearrangement, 4 nucleophilic substitution, 5 1,4-additions to enynes, 6 sigmatropic rearrangements, 7 and other methods. 8 While most of these methods usually construct mono-substituted, disubstituted or trisubstituted allenes, approaches to the synthesis of tetrasubstituted allenes have rarely been reported, especially functionalized tetrasubstituted allenes.…”

Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process

“…Due to the wide existence of allene unit in natural products, bioactive molecules 1 , and functional materials 2 , development of methods for efficient allene syntheses is of high current interest 3 – 11 . A few strategies such as allenylic substitution with 2-halo-1,3-butadienes 12 , 13 or allenyl esters 14 – 18 , 1,4-difunctionalization of 1,3-enynes 19 – 32 , allenation of the terminal alkynes (ATA) reaction 33 , 34 , and coupling reactions involving propargylic substrates 35 – 53 , have been extensively and well established.…”