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Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4747-4751. doi: 10.1002/anie.201800767. Epub 2018 Mar 25.

Visible-Light-Promoted Dearomative Fluoroalkylation of β-Naphthols through Intermolecular Charge Transfer.

Author information

1
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000, China.

Abstract

The first visible-light-promoted dearomative fluoroalkylation of β-naphthols was realized without the assistance of any transition-metal catalysts or external photosensitizers. Inexpensive fluoroalkyl iodides were directly used as efficient fluoroalkylation reagents under very mild reaction conditions. The scope of this process was found to be general and broad, and both trifluoromethyl and perfluoroalkyl groups (-C4 F9 , -C6 F13 , and -C8 F17 ) were installed in excellent yields. Preliminary mechanistic studies suggest that visible-light-promoted intermolecular charge transfer within the naphtholate-fluoroalkyl iodide electron donor-acceptor (EDA) complex induces a single electron transfer in the absence of photocatalysts.

KEYWORDS:

dearomatization; donor-acceptor complexes; fluoroalkylation; intermolecular charge transfer; β-naphthols

PMID:
29476596
DOI:
10.1002/anie.201800767

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