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

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 al...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (74), p.939-9393
Main Authors: Zhou, Zhao-Zhao, Song, Xian-Rong, Du, Sha, Xia, Ke-Jian, Tian, Wan-Fa, Xiao, Qiang, Liang, Yong-Min
Format: Article
Language:English
Subjects:
Alkylation
Carbonates
Nickel
Reagents
Regioselectivity
Substrates
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Summary: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. The first regioselective alkylation of propargylic carbonates by a photoredox/nickel dual-catalysed system for trisubstituted allenes without alkyl organometallic reagents is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03303d