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

被引：388
|
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
下载
收藏
页码：1565 / 1569
页数：5
相关论文
共 50 条
  • [21] DNA-encoded C-H functionality via photoredox-mediated hydrogen atom transformation catalysis
    Shan, Jinming
    Ling, Xing
    Liu, JiaXiang
    Wang, Xuan
    Lu, Xiaojie
    BIOORGANIC & MEDICINAL CHEMISTRY, 2021, 42
  • [22] Photoredox-Catalyzed C-H Functionalization Reactions
    Holmberg-Douglas, Natalie
    Nicewicz, David A.
    CHEMICAL REVIEWS, 2022, 122 (02) : 1925 - 2016
  • [23] Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction
    Zhang, Yongqiang
    Teuscher, Kevin B.
    Ji, Haitao
    CHEMICAL SCIENCE, 2016, 7 (03) : 2111 - 2118
  • [24] Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis
    Shah, Sk. Sheriff
    Shee, Maniklal
    Singh, Amit Kumar
    Paul, Amrita
    Singh, N. D. Pradeep
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3426 - 3439
  • [25] Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation
    Delcamp, Jared H.
    White, M. Christina
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) : 15076 - 15077
  • [26] Metal-Free Direct α-Selective Arylation of Boron Dipyrromethenes via Base-Mediated C-H Functionalization
    Zhou, Xin
    Wu, Qinghua
    Yu, Yang
    Yu, Changjiang
    Hao, Erhong
    Wei, Yun
    Mu, Xiaolong
    Jiao, Lijuan
    ORGANIC LETTERS, 2016, 18 (04) : 736 - 739
  • [27] New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction
    Singh, Parvinder Pal
    Gudup, Satish
    Aruri, Hariprasad
    Singh, Umed
    Ambala, Srinivas
    Yadav, Mahipal
    Sawant, Sanghapal D.
    Vishwakarma, Ram A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (08) : 1587 - 1597
  • [28] C-H functionalization of (hetero)arenes: Direct selanylation mediated by Selectfluor
    Belladona, Andrei L.
    Cervo, Rodrigo
    Alves, Diego
    Barcellos, Thiago
    Cargnelutti, Roberta
    Schumacher, Ricardo F.
    TETRAHEDRON LETTERS, 2020, 61 (26)
  • [29] Direct C-H Functionalization of Enamides and Enecarbamates by Using Visible-Light Photoredox Catalysis
    Jiang, Heng
    Huang, Chengmei
    Guo, Jiajia
    Zeng, Chuanqi
    Zhang, Yan
    Yu, Shouyun
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) : 15158 - 15166
  • [30] Direct photocatalytic C-H functionalization mediated by a molybdenum dioxo complex
    Baumberger, Courtney L.
    Valley, Victoria Z.
    Chambers, Matthew B.
    CHEMICAL COMMUNICATIONS, 2024, 60 (54) : 6901 - 6904
12345