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Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles.

ABSTRACT: A sequence consisting of palladium-catalyzed benzamide ortho-arylation/reaction with (CF3CO)2O was developed allowing a convenient one-pot synthesis of ortho-arylated benzonitriles and fluorenone derivatives. The outcome of this transformation is dependent on the amide N-alkyl substituent. Dehydration of ortho-arylated N-cyclohexyl-benzamides by (CF3CO)2O results in efficient production of benzonitriles. In contrast, o-arylated N-propylbenzamides are converted to fluorenone derivatives.

SUBMITTER: Shabashov D

PROVIDER: S-EPMC2627405 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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Carbon-hydrogen bond functionalization approach for the synthesis of fluorenones and ortho-arylated benzonitriles.

Shabashov Dmitry D Maldonado Jesús R Molina JR Daugulis Olafs O

The Journal of organic chemistry 20080903 19

A sequence consisting of palladium-catalyzed benzamide ortho-arylation/reaction with (CF3CO)2O was developed allowing a convenient one-pot synthesis of ortho-arylated benzonitriles and fluorenone derivatives. The outcome of this transformation is dependent on the amide N-alkyl substituent. Dehydration of ortho-arylated N-cyclohexyl-benzamides by (CF3CO)2O results in efficient production of benzonitriles. In contrast, o-arylated N-propylbenzamides are converted to fluorenone derivatives. ...[more]

PMID: 18763824

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