Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts
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| Title: | Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts |
| Author: | Pérez Saavedra, Borja Vázquez Galiñanes, Nuria Saá, Carlos Fañanás Mastral, Martín |
| Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Subject: | Alkynes | Carbocations | Copper | Diaryliodonium salts | Phosphonates | |
| Date of Issue: | 2017-08-02 |
| Publisher: | American Chemical Society |
| Citation: | Borja Pérez-Saavedra, Nuria Vázquez-Galiñanes, Carlos Saá, and Martín Fañanás-Mastral ACS Catalysis 2017 7 (9), 6104-6109 DOI: 10.1021/acscatal.7b02434 |
| Abstract: | A copper-catalyzed tandem carboarylation/cyclization of alkynyl phosphonates with diaryliodonium salts is reported. The reaction gives straightforward access to valuable cyclic enol phosphonates in good yields under mild conditions. This transformation entails an initial chemoselective arylation of the alkyne followed by an intramolecular trapping of an intermediate vinyl cation by the phosphoryl group. Observation of β-aryl rearrangements across the double bond in intermediates generated from 1,2-diaryl alkynes support the intermediacy of a vinyl cation |
| Publisher version: | https://doi.org/10.1021/acscatal.7b02434 |
| URI: | http://hdl.handle.net/10347/16980 |
| DOI: | 10.1021/acscatal.7b02434 |
| E-ISSN: | 2155-5435 |
| Rights: | © 2017 American Chemical Society |
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