4.7 Article

A Mild and Regioselective Route to Fluoroalkyl Aromatic Compounds via Directed Cycloaddition Reactions

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 15, Pages 9764-9768

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00800

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We report a mild and regiospecific boron-directed benzannulation method for accessing a range of perfluoroalkyl-substituted (hetero)aromatic building blocks, which can be easily elaborated through established C-B bond functionalization processes.
ABSTRACT: The synthesis of perfluoroalkyl-substituted (hetero)arenes by benzannulation strategies is complementary to ring functionalization approaches as it obviates the need for preexisting functionality and innate regiocontrol. We report a mild and regiospecific borondirected benzannulation method as a vehicle for accessing a range of perfluoroalkyl-substituted (hetero)aromatic building blocks that can be readily elaborated through established C-B bond functionalization processes.

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