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Synthesis 2010(13): 2245-2253  
DOI: 10.1055/s-0029-1220010
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Ruthenium-Catalyzed C-H Bond Functionalizations of 1,2,3-Triazol-4-yl-Substituted Arenes: Dehydrogenative Couplings Versus Direct Arylations

Lutz Ackermann*, Petr Novák, Rubén Vicente, Valentina Pirovano, Harish K. Potukuchi
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)396777; e-Mail: Lutz.Ackermann@chemie.uni-goettingen.de;
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Publication History

Received 18 April 2010
Publication Date:
18 May 2010 (online)

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Abstract

The chemoselectivity of ruthenium-catalyzed C-H bond arylations on triazol-4-yl-substituted arenes was found to depend on the substitution pattern of both substrates. While various aryl chlorides led to products stemming from direct arylations, ortho-substituted aryl halides in combination with ortho-alkylated arenes preferentially resulted in oxidative homo-couplings.

Key words

arylations - C-H activation - dehydrogenation - ruthenium - triazoles

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The use of other sacrificial oxidants, such as Cu(OAc)2, Ag2O, benzoquinone, [t-BuO]2, or allyl acetate, did not meet with success, under otherwise identical reaction conditions.