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: corinnas
umich.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
