Metal-free domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes: A facile access to oxybis(2-aryltetrahydrofuran) derivatives. Issue 15 (10th April 2020)

• Record Type: Journal Article
• Authors: Dey, Raghunath; Rajput, Shruti; Banerjee, Prabal
• Is Part Of: Tetrahedron. Volume 76:Issue 15(2020)
• Publication Date: 2020-04-10
• Subjects: Cyclopropanes -- Metal-free -- PTSA -- Domino reaction -- Oxybis(2-aryltetrahydrofuran) derivatives; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131080
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In this work, we have demonstrated a metal-free transformation of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives via a domino Cloke-Wilson rearrangement-hydration-dimerization sequence. Commercially inexpensive p -toluene sulfonic acid (PTSA) was used as a Brønsted acid catalyst, and reactions were conducted in an open-flask. Detection of reaction intermediates were carried to get an insight into the reaction pathway. Graphical abstract: Image 1 Highlights: A domino Cloke-Wilson rearrangement-hydration-dimerization of cyclopropane carbaldehydes to oxybis(2-aryltetrahydrofuran) derivatives. Metal-free and open-flask reaction conditions. Reactions enabled by commercially inexpensive p -toluene sulfonic acid (PTSA) as a Bronsted acid catalyst.