Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach

被引：40

作者：

Bartolomeu, Aloisio de A. ^{[1
,2
]}

Silva, Rodrigo C. ^{[1
]}

Brocksom, Timothy J. ^{[1
]}

Noel, Timothy ^{[2
]}

de Oliveira, Kleber T. ^{[1
]}

机构：

[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil

[2] Eindhoven Univ Technol, Dept Chem Engn & Chem, Sustainable Proc Engn, Micro Flow Chem & Synthet Methodol, De Rondom 70,STO 1-37, NL-5612 AP Eindhoven, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 16期

基金：

巴西圣保罗研究基金会;

关键词：

C-H ARYLATION; ELECTRON-DEFICIENT HETEROCYCLES; SUZUKI-MIYAURA REACTION; (HETERO)ARYL CHLORIDES; NITROGEN-HETEROCYCLES; DIARYLIODONIUM SALTS; PHOTOREDOX CATALYSIS; PALLADIUM CATALYST; RADICAL ARYLATION; COUPLING REACTION;

D O I：

10.1021/acs.joc.9b01879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96%. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.

引用

收藏

页码：10459 / 10471

页数：13

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