Brønsted Acid Catalyzed Direct Annulation of Alkoxyallenes and Naphthols to Chroman Ketals

Abstract

A straightforward Brønsted acid-catalyzed and scalable annulation of alkoxyallenes with simple naphthols was developed, affording chroman ketals in 49–84% yields. The versatile chroman ketals can be easily converted into coumarins by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidation, and a series of 2-substituted chromans via nucleophilic substitutions.

Key words

Brønsted acids - annulation - chroman ketal - coumarin - chroman

Publication History

Received: 01 December 2021

Accepted after revision: 20 December 2021

Article published online:
14 February 2022

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