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Literature DB >> 31411869

C-N Cross-Couplings for Site-Selective Late-Stage Diversification via Aryl Sulfonium Salts.

Pascal S Engl¹, Andreas P Häring¹, Florian Berger¹, Georg Berger¹, Alberto Pérez-Bitrián¹, Tobias Ritter¹.

Abstract

We report diverse C-N cross-coupling reactions of aryl thianthrenium salts that are formed site-selectively by direct C-H functionalization. The scope of N-nucleophiles ranges from primary and secondary alkyl and aryl amines to various N-containing heterocycles, and the overall transformation is applicable to late-stage functionalization of complex, drug-like small molecules.

Entities: Chemical

Year: 2019 PMID： 31411869 DOI： 10.1021/jacs.9b07323

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

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Cited

20 in total

1. Thianthrenium-Enabled Sulfonylation via Electron Donor-Acceptor Complex Photoactivation.

Authors: Albert Granados; María Jesús Cabrera-Afonso; Marcos Escolano; Shorouk O Badir; Gary A Molander
Journal: Chem Catal Date: 2022-04-05

2. Red Light-Based Dual Photoredox Strategy Resembling the Z-Scheme of Natural Photosynthesis.

Authors: Felix Glaser; Oliver S Wenger
Journal: JACS Au Date: 2022-06-10

3. Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts.

Authors: María Jesús Cabrera-Afonso; Albert Granados; Gary A Molander
Journal: Angew Chem Int Ed Engl Date: 2022-03-30 Impact factor: 16.823

4. Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

Authors: Beatrice Lansbergen; Paola Granatino; Tobias Ritter
Journal: J Am Chem Soc Date: 2021-05-24 Impact factor: 15.419

5. Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF₃⁺, CF₃^•, and CF₃^- Reactivity.

Authors: Hao Jia; Andreas P Häring; Florian Berger; Li Zhang; Tobias Ritter
Journal: J Am Chem Soc Date: 2021-05-14 Impact factor: 15.419

C-N Cross-Couplings for Site-Selective Late-Stage Diversification via Aryl Sulfonium Salts.

1. Thianthrenium-Enabled Sulfonylation via Electron Donor-Acceptor Complex Photoactivation.

2. Red Light-Based Dual Photoredox Strategy Resembling the Z-Scheme of Natural Photosynthesis.

3. Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts.

4. Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

5. Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF₃⁺, CF₃^•, and CF₃^- Reactivity.

6. Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides.

7. Site-Selective Late-Stage Aromatic [¹⁸ F]Fluorination via Aryl Sulfonium Salts.

8. Synthesis, Structure, and Reactivity of 5-(Aryl)dibenzothiophenium Triflates.

9. Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication.

10. Regio- and Stereoselective Thianthrenation of Olefins To Access Versatile Alkenyl Electrophiles.