Photoredox/nickel dual-catalyzed regioselective alkylation of propargylic carbonates for trisubstituted allenes. Issue 74 (24th August 2021)

• Record Type: Journal Article
• Authors: Zhou, Zhao-Zhao; Song, Xian-Rong; Du, Sha; Xia, Ke-Jian; Tian, Wan-Fa; Xiao, Qiang; Liang, Yong-Min
• Is Part Of: Chemical communications. Volume 57:Issue 74(2021)
• Page Start: 9390
• Page End: 9393
• Publication Date: 2021-08-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc03303d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The first regioselective alkylation of propargylic carbonates by a photoredox/nickel dual-catalysed system for trisubstituted allenes without alkyl organometallic reagents is described. Abstract : 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.