Photoredox-catalyzed selective head-to-head reductive coupling of activated alkenes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-01-25 DOI:10.1039/d4qo02344g

Shenhao Chen, Zongchang Han, Han-Shi Hu, Jun Li, Chanjuan Xi

引用次数: 0

Abstract

Head-to-head reductive hydrodimerization of activated alkenes offers access to valuable bulk or fine chemicals, such as adipates or adiponitrile as an intermediate for industrial synthesis of nylon. We herein report a novel reaction to realize head-to-head reductive coupling of activated alkenes by a photoinduced Ir/PPh₃/H₂O system, providing mild access to various adipate derivatives in high chemo- and regioselectivity. In this reaction, a [Ph₃P-OH] radical generated from a photoinduced interaction between H₂O and PPh₃ enables the PCET process with activated alkenes to form C-centered radical at the β-position that is rarely reported.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.