Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 74, Pages 9390-9393Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc03303d
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Funding
- Nanchang Normal University [NSBSJJ2020009]
- Science and Technology Program of Department of Education, Jiangxi Province [GJJ202630]
- National Natural Science Foundation of China [22001101]
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A highly regioselective alkylation method for trisubstituted allenes with alkyl 1,4-dihydropyridine derivatives has been developed through a photoredox/nickel dual-catalyzed process, providing alkylated allene products without the need for alkyl organometallic reagents. The method shows a broad substrate scope and mild reaction conditions, with potential applications in pharmaceutical synthesis.
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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