Ag(i)-Promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes via a [4 + 2] cycloaddition of benzopyrylium ions: access to structurally unique naphthalenes. Issue 1 (14th December 2021)

• Record Type: Journal Article
• Authors: Baire, Beeraiah; Santhi, Jampani
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 1(2021)
• Page Start: 247
• Page End: 251
• Publication Date: 2021-12-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02229f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Discovery and development of a Ag(i )-promoted, homodimerization of benzopyrylium ions (generated from 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes) via a [4 + 2] cycloaddition, for the synthesis of naphthalenes is reported. Abstract : Herein we report a Ag(i )-promoted homo-dimerization of 2-(alk-2-yn-1-onyl)-1-alkynylbenzenes for the synthesis of structurally novel and functionalized naphthalene derivatives. This transformation exhibits a broad scope for the alkyl as well as aryl groups present on alkynes. Observations made from control experiments suggest the possible mechanism as (i) the homo-dimerization of the in situ generated benzopyrylium ion intermediates through a head–tail [4 + 2] cycloaddition, followed by (ii) the competitive ring-opening vs . decarbonylative aromatization of the adduct to give formylated and deformylated naphthalenes, respectively.