Accessing meta-Enone-Substituted Anisoles using ArN₂BF₄ as Precatalyst via Rearrangement of Alkyne-Tethered Cyclohexadienones

Abstract

A method for the rearrangement of alkyne-tethered cyclohexadienone to furnish meta-enone-substituted anisoles using arene diazonium tetrafluoroborate salts as precatalyst was developed. The reaction proceeds via intramolecular 1,6-enyne cyclization-aromatization and oxetene ring opening. The same protocol was also employed to obtain phthalide-substituted anisoles. The reactions are atom economic, have a broad substrate scope and amenable to gram-scale synthesis. Further synthetic transformations of the products were also performed.

Key words

rearrangement - diazonium salt - alkyne-tethered cyclohexadienone - substituted anisoles

Publication History

Received: 22 March 2024

Accepted after revision: 23 May 2024

Accepted Manuscript online:
23 May 2024

Article published online:
11 June 2024

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