Tags

Type your tag names separated by a space and hit enter

A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives.
J Org Chem. 2004 Nov 26; 69(24):8258-65.JO

Abstract

Treatment of various types of fluoroalkylated alkynes with o-iodoaniline in the presence of Pd(PPh(3))(4) in DMF at 80 degrees C for 8 h mainly gave 2-fluoroalkylated indoles in high yields. The use of P(o-Tol)(3) instead of PPh(3) as a ligand led to the preferential formation of 3-fluoroalkylated indoles in high yields. Interestingly, the reaction of trifluoromethylated alkynes bearing a benzylic substituent afforded 2- or 3-trifluoroethylated indole derivatives in good yields.

Authors+Show Affiliations

Konno T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
Chae J
No affiliation info available
Ishihara T
No affiliation info available
Yamanaka H
No affiliation info available

MeSH

AlkynesAniline CompoundsCatalysisCyclizationFluorineIndolesModels, MolecularMolecular StructurePalladiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15549796

Citation

Konno, Tsutomu, et al. "A Facile Regiocontrol in the Palladium-catalyzed Annulation of Fluorine-containing Internal Alkynes With Variously Substituted 2-iodoanilines: a New Regioselective Synthesis of 2- or 3-fluoroalkylated Indole Derivatives." The Journal of Organic Chemistry, vol. 69, no. 24, 2004, pp. 8258-65.
Konno T, Chae J, Ishihara T, et al. A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives. J Org Chem. 2004;69(24):8258-65.
Konno, T., Chae, J., Ishihara, T., & Yamanaka, H. (2004). A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives. The Journal of Organic Chemistry, 69(24), 8258-65.
Konno T, et al. A Facile Regiocontrol in the Palladium-catalyzed Annulation of Fluorine-containing Internal Alkynes With Variously Substituted 2-iodoanilines: a New Regioselective Synthesis of 2- or 3-fluoroalkylated Indole Derivatives. J Org Chem. 2004 Nov 26;69(24):8258-65. PubMed PMID: 15549796.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives. AU - Konno,Tsutomu, AU - Chae,Jungha, AU - Ishihara,Takashi, AU - Yamanaka,Hiroki, PY - 2004/11/20/pubmed PY - 2005/1/14/medline PY - 2004/11/20/entrez SP - 8258 EP - 65 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 24 N2 - Treatment of various types of fluoroalkylated alkynes with o-iodoaniline in the presence of Pd(PPh(3))(4) in DMF at 80 degrees C for 8 h mainly gave 2-fluoroalkylated indoles in high yields. The use of P(o-Tol)(3) instead of PPh(3) as a ligand led to the preferential formation of 3-fluoroalkylated indoles in high yields. Interestingly, the reaction of trifluoromethylated alkynes bearing a benzylic substituent afforded 2- or 3-trifluoroethylated indole derivatives in good yields. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15549796/A_facile_regiocontrol_in_the_palladium_catalyzed_annulation_of_fluorine_containing_internal_alkynes_with_variously_substituted_2_iodoanilines:_a_new_regioselective_synthesis_of_2__or_3_fluoroalkylated_indole_derivatives_ DB - PRIME DP - Unbound Medicine ER -