Transition metal catalyzed C-H arylation is an efficient strategy for the formation of biaryls from C-H bonds. Among the many available directing groups utilized for this transformation, naphthols remain underdeveloped. A general approach for the peri-arylation of 1-naphthol would allow for the rapid generation of 1,8-substituted naphthols. These disubstituted naphthols are useful molecules for organic light emitting diode (OLED) materials, as well as intermediates en route to fluoranthene derivatives. New conditions will be presented for the directed C-H arylation of 1-naphthol utilizing a variety of aryl and heteroaryl halides (iodides, bromides). This system employs the hydroxyl group of the naphthol as a directing group for this transformation in the presence of a ruthenium catalyst. The conditions are tolerant of many functional groups on the arylating agent, including free amines, trifluoromethyl groups, thiols, methyl esters, pyrans, and aldehydes. Quinoline, pyridines, and pyrazines can also be incorporated in these arylation reactions.

Ruthenium-catalyzed C-H arylation of 1-naphthol with aryl and heteroaryl halides

256th National Meeting (2018)

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