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Synthesis 2010(13): 2245-2253
DOI: 10.1055/s-0029-1220010
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
Weitere Informationen
Received
18 April 2010
Publikationsdatum:
18. Mai 2010 (online)
Publikationsverlauf
Publikationsdatum:
18. Mai 2010 (online)
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.