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Synthesis of Benzo[]furans from Alkynyl Sulfoxides and Phenols by the Interrupted Pummerer Reaction

Overview
Journal RSC Adv
Specialty Chemistry
Date 2023 Jan 23
PMID 36686947
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Abstract

The interrupted Pummerer reaction of alkynyl sulfoxides with phenols is disclosed. A wide range of benzo[]furans were efficiently synthesized through unexplored electrophilic activation of the electron-deficient alkynyl sulfinyl group. Based on the good availability of alkynyl sulfoxides, we successfully prepared various functionalized benzo[]furans from readily available alkynes, thiosulfonates, and phenols.

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References
1.
Kobayashi A, Matsuzawa T, Hosoya T, Yoshida S . Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions. Chem Commun (Camb). 2020; 56(40):5429-5432. DOI: 10.1039/d0cc02253e. View

2.
Todorovic U, Klose I, Maulide N . Straightforward Access to Thiocyanates via Dealkylative Cyanation of Sulfoxides. Org Lett. 2021; 23(7):2510-2513. PMC: 8022320. DOI: 10.1021/acs.orglett.1c00460. View

3.
Okamoto K, Hori M, Yanagi T, Murakami K, Nogi K, Yorimitsu H . Sigmatropic Dearomatization/Defluorination Strategy for C-F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols. Angew Chem Int Ed Engl. 2018; 57(43):14230-14234. DOI: 10.1002/anie.201809035. View

4.
Wang D, Carlton C, Tayu M, McDouall J, Perry G, Procter D . Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation. Angew Chem Int Ed Engl. 2020; 59(37):15918-15922. PMC: 7540508. DOI: 10.1002/anie.202005531. View

5.
Ookubo Y, Wakamiya A, Yorimitsu H, Osuka A . Synthesis of a library of fluorescent 2-aryl-3-trifluoromethylnaphthofurans from naphthols by using a sequential pummerer-annulation/cross-coupling strategy and their photophysical properties. Chemistry. 2012; 18(40):12690-7. DOI: 10.1002/chem.201201261. View