Direct α-Arylation of Ethers through the Combination of Photoredox-Mediated C-H Functionalization and the Minisci Reaction

被引：399

作者：

Jin, Jian ^{[1
]}

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

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 05期

关键词：

alkylation; C-H functionalization; ethers; heterocycles; photoredox catalysis; FREE-RADICAL REACTIONS; NUCLEOPHILIC CHARACTER; ALKYL RADICALS; HETEROAROMATIC BASES; RATE CONSTANTS; SINGLE-LAYER; LIGHT; CATALYSIS; PHOTOCHEMISTRY; PHOTOPHYSICS;

D O I：

10.1002/anie.201410432

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct alpha-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated C-H functionalization pathway. Transiently generated alpha-oxyalkyl radicals, produced from a variety of widely available ethers through hydrogen atom transfer (HAT), were coupled with a range of electron-deficient heteroarenes in a Minisci-type mechanism. This mild, visible-light- driven protocol allows direct access to medicinal pharmacophores of broad utility using feedstock substrates and a commercial photocatalyst.

引用

页码：1565 / 1569

页数：5

共 50 条

[31] The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis
Cuthbertson, James D.
MacMillan, David W. C.
NATURE, 2015, 519 (7541) : 74 - 77
[32] Photoredox C-H arylation of heteroarenes by high-efficiency bismuth quantum dots
Huang, Zhihui
Zhu, Jun
Dong, Qing
Huang, Qingqiu
Wang, Mengke
Zhu, Youhua
Huang, Weichun
Zi, You
TETRAHEDRON LETTERS, 2023, 127
[33] The Combination of Benzaldehyde and Nickel-Catalyzed Photoredox C(sp3)-H Alkylation/Arylation
Zhang, Lumin
Si, Xiaojia
Yang, Yangyang
Zimmer, Marc
Witzel, Sina
Sekine, Kohei
Rudolph, Matthias
Hashmi, A. Stephen K.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) : 1823 - 1827
[34] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
Condie, Allison G.
Gonzalez-Gomez, Jose C.
Stephenson, Corey R. J.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
[35] Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
Wang, Bang
Xiong, De-Cai
Ye, Xin-Shan
ORGANIC LETTERS, 2015, 17 (22) : 5698 - 5701
[36] Unlocking C-H Functionalization at Room Temperature via a Light-Mediated Protodemetalation Reaction
Empel, Claire
Jana, Sripati
Koodan, Adithyaraj
Koenigs, Rene M.
ACS CATALYSIS, 2022, 12 (14) : 8229 - 8236
[37] Metal-, Photocatalyst-, and Light-Free Minisci C-H Acetylation of N-Heteroarenes with Vinyl Ethers
Dong, Jianyang
Liu, Jianhua
Song, Hongjian
Liu, Yuxiu
Wang, Qingmin
ORGANIC LETTERS, 2021, 23 (11) : 4374 - 4378
[38] Minisci-Type C-H Cyanoalkylation of Heteroarenes Through N-O/C-C Bonds Cleavage
Jian, Yong
Chen, Ming
Yang, Chao
Xia, Wu-jiong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1439 - 1442
[39] Silver-catalyzed direct selenylation of terminal alkynes through C-H bond functionalization
Xavier, Mauricio C. D. F.
Goldani, Bruna
Schumacher, Ricardo F.
Perin, Gelson
Schneider, Paulo Henrique
Alves, Diego
MOLECULAR CATALYSIS, 2017, 427 : 73 - 79
[40] Visible Light Photoredox Catalysis: Investigation of Distal sp3 C-H Functionalization of Tertiary Amines for Alkylation Reaction
Pandey, Ganesh
Jadhav, Deepak
Tiwari, Sandip Kumar
Singh, Bhawana
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2813 - 2818

← 1 2 3 4 5 →