Synergistic Pd/Ag-Catalyzed Domino Reaction: Access to Tetrahydropyrano[4,3-c]pyran and Hexahydrofuro[2,3-b]pyran

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-28 DOI:10.1021/acs.orglett.5c00018

Dipak B. Deokar, Roumi Patra, Y. Bhargav Kumar, B. Sridhar, Yarasi Soujanya, Pravin R. Likhar

引用次数: 0

Abstract

We report the Pd-catalyzed and Ag-mediated temperature-dependent divergent synthesis of tetrahydropyrano[4,3-c]pyran and hexahydrofuro[2,3-b]pyran derivatives from a single substrate, alkynols. The reaction involves homocoupling of alkynols to form two C–O bonds and one C–C bond, resulting in tetrahydropyrano[4,3-c]pyran cores at a high temperature (110 °C). Exposing tetrahydropyrano[4,3-c]pyrans to a 200 W tungsten filament bulb yields tetrahydrofuro[2,3-b]pyrans. At lower temperatures (30–60 °C), alkynols produce hexahydrofuro[2,3-b]pyrans. The density functional theory study explains temperature-dependent selectivity.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.