Metallaphotoredox Difluoromethylation of Aryl Bromides

被引：153

作者：

Bacauanu, Vlad ^{[1
]}

Cardinal, Sebastien ^{[1
]}

Yamauchi, Motoshi ^{[1
]}

Kondo, Masaru ^{[1
]}

Fernandez, David F. ^{[1
]}

Remy, Richard ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Washington Rd, Princeton, NJ 08544 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 38期

基金：

瑞士国家科学基金会;

关键词：

difluoromethylation; fluorine; heterocycles; nickel; photoredox catalysis; PALLADIUM-CATALYZED DIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; FLUORINE; PHOTOREDOX; HALIDES; DERIVATIVES; CHLORIDES; IODIDES;

D O I：

10.1002/anie.201807629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report a convenient and broadly applicable strategy for the difluoromethylation of aryl bromides by metallaphotoredox catalysis. Bromodifluoromethane, a simple and commercially available alkyl halide, is harnessed as an effective source of difluoromethyl radical by silyl-radical-mediated halogen abstraction. The merger of this fluoroalkyl electrophile activation pathway with a dual nickel/photoredox catalytic platform enables the difluoromethylation of a diverse array of aryl and heteroaryl bromides under mild conditions. The utility of this procedure is show cased in the late-stage functionalization of several drug analogues.

引用

页码：12543 / 12548

页数：6

共 43 条

[41] Profiling and Application of Photoredox C(sp3)-C(sp2) Cross-Coupling in Medicinal Chemistry [J].

Zhang, Rui ;

Li, Guoqing ;

Wismer, Michael ;

Vachal, Petr ;

Colletti, Steven L. ;

Shi, Zhi-Cai .

ACS MEDICINAL CHEMISTRY LETTERS, 2018, 9 (07) :773-777

[42]

Zhuo Y., 2016, CHEM REV, V116, P422

[43] Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides [J].

Zuo, Zhiwei ;

Ahneman, Derek T. ;

Chu, Lingling ;

Terrett, Jack A. ;

Doyle, Abigail G. ;

MacMillan, David W. C. .

SCIENCE, 2014, 345 (6195) :437-440

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