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Literature DB >> 28098990

Chemo- and Regioselective Distal Heteroaryl ipso-Migration: A General Protocol for Heteroarylation of Unactivated Alkenes.

Zhen Wu¹, Dongping Wang¹, Yuan Liu¹, Leitao Huan¹, Chen Zhu¹.

Abstract

Herein we report a novel, general protocol for distal heteroaryl ipso-migration and its application to the elusive heteroarylation of unactivated alkenes. A set of nitrogen-containing heteroaryl groups showcase the migratory aptitude. This reaction provides a variety of fluoroalkyl functionalized heteroarenes under mild reaction conditions. This is the first report of a difunctionalization of unactivated alkenes with distal heteroaryl migration.

Entities: Chemical

Year: 2017 PMID： 28098990 DOI： 10.1021/jacs.6b11234

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

14 in total

1. A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO₂F radical reagent.

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Journal: Nat Commun Date: 2022-06-18 Impact factor: 17.694

Review 2. Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

Authors: Anthony R Allen; Efrey A Noten; Corey R J Stephenson
Journal: Chem Rev Date: 2021-10-21 Impact factor: 72.087

3. Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

Authors: Satavisha Sarkar; Arghya Banerjee; Wang Yao; Eric V Patterson; Ming-Yu Ngai
Journal: ACS Catal Date: 2019-10-17 Impact factor: 13.084

4. CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na.

Authors: Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal: Beilstein J Org Chem Date: 2017-12-19 Impact factor: 2.883

10. Dye-incorporated coordination polymers for direct photocatalytic trifluoromethylation of aromatics at metabolically susceptible positions.

Authors: Tiexin Zhang; Xiangyang Guo; Yusheng Shi; Cheng He; Chunying Duan
Journal: Nat Commun Date: 2018-10-02 Impact factor: 14.919

Chemo- and Regioselective Distal Heteroaryl ipso-Migration: A General Protocol for Heteroarylation of Unactivated Alkenes.

1. A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO₂F radical reagent.

Review 2. Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer.

3. Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

4. CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na.

5. Alkene 1,2-Difunctionalization by Radical Alkenyl Migration.

6. α-Perfluoroalkyl-β-alkynylation of alkenes via radical alkynyl migration.

7. Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis.

8. Radical Aryl Migration from Boron to Carbon.

9. Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

10. Dye-incorporated coordination polymers for direct photocatalytic trifluoromethylation of aromatics at metabolically susceptible positions.