Literature DB >> 29966092

Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations.

William Lecroq1, Pierre Bazille1, Fabrice Morlet-Savary2, Martin Breugst3, Jacques Lalevée2, Annie-Claude Gaumont1, Sami Lakhdar1.   

Abstract

This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.

Entities:  

Year:  2018        PMID: 29966092     DOI: 10.1021/acs.orglett.8b01379

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

Authors:  Feiyang Xu; Olivia M Duke; Daniel Rojas; Hanka M Eichelberger; Raphael S Kim; Timothy B Clark; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-07-02       Impact factor: 15.419

2.  I2-mediated Csp2-P bond formation via tandem cyclization of o-alkynylphenyl isothiocyanates with organophosphorus esters.

Authors:  Yang Liu; Wenjin Wu; Xiaoyan Sang; Yu Xia; Guojian Fang; Wenyan Hao
Journal:  RSC Adv       Date:  2022-06-20       Impact factor: 4.036

3.  Visible Light-Enabled sp3 -C-H Functionalization with Chloro- and Bromoalkynes: Chemoselective Route to Vinylchlorides or Alkynes.

Authors:  Tapas Adak; Marvin Hoffmann; Sina Witzel; Matthias Rudolph; Andreas Dreuw; A Stephen K Hashmi
Journal:  Chemistry       Date:  2020-10-15       Impact factor: 5.236

4.  C-P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds.

Authors:  Simon Oßwald; Christoph Zippel; Zahid Hassan; Martin Nieger; Stefan Bräse
Journal:  RSC Adv       Date:  2022-01-25       Impact factor: 3.361

5.  The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols.

Authors:  Yuvraj Satkar; Kazimierz Wrobel; Daniel E Trujillo-González; Rafael Ortiz-Alvarado; J Oscar C Jiménez-Halla; César R Solorio-Alvarado
Journal:  Front Chem       Date:  2020-10-15       Impact factor: 5.221

  5 in total

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