Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible-Light Photoredox Catalysis

被引：70

作者：

Claros, Miguel ^{[1
]}

Ungeheuer, Felix ^{[1
]}

Franco, Federico ^{[1
]}

Martin-Diaconescu, Vlad ^{[1
]}

Casitas, Alicia ^{[1
]}

Lloret-Fillol, Julio ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Avda Paisos Catalans 16, Tarragona 43007, Spain

[2] Catalan Inst Res & Adv Studies ICREA, Passeig Lluis Co 23, Barcelona 08010, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 15期

基金：

欧洲研究理事会;

关键词：

cyclizations; haloalkanes; photochemistry; reaction mechanisms; synthetic methods; METAL-COMPLEXES; BOND FORMATION; ARYL HALIDES; VITAMIN-B12; MODEL; FUNCTIONALIZATION; ELECTROREDUCTION; TRANSFORMATIONS; CARBOXYLATION; REARRANGEMENT;

D O I：

10.1002/anie.201812702

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chemical inertness of abundant and commercially available alkyl chlorides precludes their widespread use as reactants in chemical transformations. Presented in this work is a metallaphotoredox methodology to achieve the catalytic intramolecular reductive cyclization of unactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp(3))-Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer. The high basicity and multidentate nature of the ligands are key to obtaining efficient metal catalysts for the functionalization of unactivated alkyl chlorides.

引用

页码：4869 / 4874

页数：6

共 63 条

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