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Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.

ABSTRACT: While 8-aryl-1-napthols are promising dye molecules and useful intermediates in the synthesis of polycyclic aromatic hydrocarbons, they can be difficult to access. A new, ruthenium-catalyzed method for peri-C-H arylation of 1-naphthol with a variety of aryl and heteroaryl halides (iodides, bromides) is reported that overcomes the limitations of previous palladium-catalyzed approaches. Yields for the 21 examples range from 16 to 99%, with an average of 71%, and the reaction tolerates a variety of functional groups: pyridine, pyrimidine, primary aniline, aldehyde, and ester.

SUBMITTER: Spiewak AM

PROVIDER: S-EPMC6905617 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.

Spiewak Amanda M AM Weix Daniel J DJ

The Journal of organic chemistry 20191125 23

While 8-aryl-1-napthols are promising dye molecules and useful intermediates in the synthesis of polycyclic aromatic hydrocarbons, they can be difficult to access. A new, ruthenium-catalyzed method for <i>peri</i>-C-H arylation of 1-naphthol with a variety of aryl and heteroaryl halides (iodides, bromides) is reported that overcomes the limitations of previous palladium-catalyzed approaches. Yields for the 21 examples range from 16 to 99%, with an average of 71%, and the reaction tolerates a var ...[more]

PMID: 31725290

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