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Literature DB >> 18763824

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

Dmitry Shabashov¹, Jesús R Molina Maldonado, Olafs Daugulis.

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.

Entities: Chemical Disease Gene

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Year: 2008 PMID： 18763824 PMCID： PMC2627405 DOI： 10.1021/jo801300y

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

49 in total

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Authors: N Chatani; A Kamitani; M Oshita; Y Fukumoto; S Murai
Journal: J Am Chem Soc Date: 2001-12-19 Impact factor: 15.419

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Authors: Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

3. Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors: Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal: Chem Rev Date: 2002-05 Impact factor: 60.622

4. A Convenient Synthesis of Dengibsin.

Authors: Winton D. Jones; Fred L. Ciske
Journal: J Org Chem Date: 1996-05-31 Impact factor: 4.354

5. Synthesis of 2-(2,3-dimethoxyphenyl)-4-(aminomethyl)imidazole analogues and their binding affinities for dopamine D(2) and D(3) receptors.

Authors: Y Huang; R R Luedtke; R A Freeman; L Wu; R H Mach
Journal: Bioorg Med Chem Date: 2001-12 Impact factor: 3.641

6. New diarylmethylpiperazines as potent and selective nonpeptidic delta opioid receptor agonists with increased In vitro metabolic stability.

Authors: N Plobeck; D Delorme; Z Y Wei; H Yang; F Zhou; P Schwarz; L Gawell; H Gagnon; B Pelcman; R Schmidt; S Y Yue; C Walpole; W Brown; E Zhou; M Labarre; K Payza; S St-Onge; A Kamassah; P E Morin; D Projean; J Ducharme; E Roberts
Journal: J Med Chem Date: 2000-10-19 Impact factor: 7.446

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

1. Catalytic carbonylation reactions of benzyne derivatives.

2. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

3. Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

4. A Convenient Synthesis of Dengibsin.

5. Synthesis of 2-(2,3-dimethoxyphenyl)-4-(aminomethyl)imidazole analogues and their binding affinities for dopamine D(2) and D(3) receptors.

6. New diarylmethylpiperazines as potent and selective nonpeptidic delta opioid receptor agonists with increased In vitro metabolic stability.

7. Ruthenium complex-catalyzed direct ortho arylation and alkenylation of 2-arylpyridines with organic halides.

8. Synthesis of fluoren-9-ones via palladium-catalyzed cyclocarbonylation of o-halobiaryls.

9. Annulation strategies for benzo[b]fluorene synthesis: efficient routes to the kinafluorenone and WS-5995 antibiotics.

10. Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls.

Review 1. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.

Review 2. Palladium-catalyzed ligand-directed C-H functionalization reactions.

3. O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization.

4. Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.