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

Zhao-Zhao ZhouXian-Rong SongSha DuKe-Jian XiaWan-Fa TianQiang XiaoYong-Min Liang
Published in: Chemical communications (Cambridge, England) (2021)
Herein, a highly regioselective alkylation of propargylic carbonates for trisubstituted allenes with alkyl 1,4-dihydropyridine derivatives (1,4-DHPs) is developed via a photoredox/nickel dual-catalyzed process, which represents the first direct approach to access alkylated allene products without alkyl organometallic reagents. This method features a broad substrate scope and mild conditions. A hypothetical mechanism with an alkyl radical and an allenyl Ni(III) species is proposed. Benzylation products were also obtained to be the complement building blocks for the potential synthesis of pharmaceuticals.
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