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Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates

Rebecca B. Watson and Corinna S. Schindler*

*Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States, Email: corinnasumich.edu

R. B. Watson, C. S. Schindler, Org. Lett., 2018, 20, 68-71.

DOI: 10.1021/acs.orglett.7b03367


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Abstract

An operational simple iron(III)-catalyzed strategy toward functionalized tetrahydronaphthalenes in high yields takes advantage of a unique reactivity observed for simple aryl ketone precursors . Detailed mechanistic investigations identified pyrans as reactive intermediates that afford the desired tetrahydronaphthalenes upon iron(III)-catalyzed Friedel-Crafts alkylation.

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proposed mechanism



Key Words

Tetrahydronaphthalenes, Friedel-Crafts Alkylation


ID: J54-Y2018