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Literature DB >> 25470570

Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

Abstract

The direct α-arylation of cyclic and acyclic ethers with heteroarenes has been accomplished through the design of a photoredox-mediated CH functionalization pathway. Transiently generated α-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.

Entities: Chemical Gene

Keywords: CH functionalization; alkylation; ethers; heterocycles; photoredox catalysis

Mesh：

Substances：
Ethers
Carbon
Hydrogen

Year: 2014 PMID： 25470570 PMCID： PMC4311771 DOI： 10.1002/anie.201410432

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

27 in total

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Authors: Jagan M R Narayanam; Corey R J Stephenson
Journal: Chem Soc Rev Date: 2010-06-08 Impact factor: 54.564

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Authors: Johannes A Burkhard; Georg Wuitschik; Mark Rogers-Evans; Klaus Müller; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2010-11-22 Impact factor: 15.336

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Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

4. 2-Lithiated-2-phenyloxetane: a new attractive synthon for the preparation of oxetane derivatives.

Authors: Donato Ivan Coppi; Antonio Salomone; Filippo Maria Perna; Vito Capriati
Journal: Chem Commun (Camb) Date: 2011-08-04 Impact factor: 6.222

Review 5. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

6. Late-stage functionalization of biologically active heterocycles through photoredox catalysis.

Authors: Daniel A Dirocco; Kevin Dykstra; Shane Krska; Petr Vachal; Donald V Conway; Matthew Tudge
Journal: Angew Chem Int Ed Engl Date: 2014-03-26 Impact factor: 15.336

7. Total syntheses of menisporphine and daurioxoisoporphine C enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium salt.

Authors: Jing Zhang; Jie Chen; Xiaoyun Zhang; Xiaoguang Lei
Journal: J Org Chem Date: 2014-10-24 Impact factor: 4.354

8. Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.

Authors: Andrew McNally; Christopher K Prier; David W C MacMillan
Journal: Science Date: 2011-11-25 Impact factor: 47.728

9. Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Authors: Chunhui Dai; Francesco Meschini; Jagan M R Narayanam; Corey R J Stephenson
Journal: J Org Chem Date: 2012-04-18 Impact factor: 4.354

10. Photoredox activation for the direct β-arylation of ketones and aldehydes.

Authors: Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal: Science Date: 2013-03-29 Impact factor: 47.728

40 in total

1. O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

Authors: Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal: Science Date: 2015-08-27 Impact factor: 47.728

2. A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

Authors: Kaila A Margrey; William L Czaplyski; David A Nicewicz; Erik J Alexanian
Journal: J Am Chem Soc Date: 2018-03-16 Impact factor: 15.419

3. Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade.

Authors: J Quentin Buquoi; Jeremy M Lear; Xin Gu; David A Nagib
Journal: ACS Catal Date: 2019-05-06 Impact factor: 13.084

Review 4. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors: Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal: Chem Rev Date: 2021-08-10 Impact factor: 60.622

Review 5. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

10. Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics.

Authors: Mahesh K Lakshman; Prasanna K Vuram
Journal: Chem Sci Date: 2017-06-30 Impact factor: 9.825