Literature DB >> 23865378

Copper-catalyzed P-arylation via direct coupling of diaryliodonium salts with phosphorus nucleophiles at room temperature.

Jian Xu1, Pengbo Zhang, Yuzhen Gao, Yiyin Chen, Guo Tang, Yufen Zhao.   

Abstract

A new method for copper-catalyzed P-C bond formation through reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature is described. Most target products are obtained with this method in high yields within a short reaction time of 10 min. It can be easily adapted to large-scale preparations. When unsymmetrical iodonium salts are employed, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.

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Year:  2013        PMID: 23865378     DOI: 10.1021/jo4012199

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 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.  Crystal Structures of Diaryliodonium Fluorides and Their Implications for Fluorination Mechanisms.

Authors:  Yong-Sok Lee; Joong-Hyun Chun; Milan Hodošček; Victor W Pike
Journal:  Chemistry       Date:  2017-03-02       Impact factor: 5.236

3.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

4.  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

5.  Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in Copper Catalysis.

Authors:  Naoko Ichiishi; Allan J Canty; Brian F Yates; Melanie S Sanford
Journal:  Organometallics       Date:  2014-09-22       Impact factor: 3.876

6.  A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis.

Authors:  Ying He; Hongmiao Wu; F Dean Toste
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

7.  Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds.

Authors:  Pauline Adler; Amandine Pons; Jing Li; Jörg Heider; Bogdan R Brutiu; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

8.  A Sustainable and Efficient Synthesis of Benzyl Phosphonates Using PEG/KI Catalytic System.

Authors:  Shamrao Disale; Sandip Kale; George Abraham; Sandeep Kahandal; Ashish N Sawarkar; Manoj B Gawande
Journal:  Front Chem       Date:  2016-08-16       Impact factor: 5.221

9.  Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.

Authors:  Rodolphe Beaud; Robert J Phipps; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2016-09-30       Impact factor: 15.419

10.  Copper-catalyzed enantioselective arylalkynylation of alkenes.

Authors:  Guangyue Lei; Hanwen Zhang; Bin Chen; Meichen Xu; Guozhu Zhang
Journal:  Chem Sci       Date:  2020-01-08       Impact factor: 9.825

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