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ABSTRACT: [reaction: see text] The palladium-catalyzed annulation reaction of fluoroalkylated alkynes with various 2-iodobenzylidenamines was investigated. In the presence of a catalytic amount of Pd(PPh3)4, the reaction took place smoothly to give the corresponding 4-fluoroalkylated isoquinoline in high yield as a single isomer. No other regioisomer was detected.
The Journal of Organic Chemistry 12/2005; 70(24):10172-4. · 4.45 Impact Factor
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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.
The Journal of Organic Chemistry 12/2004; 69(24):8258-65. · 4.45 Impact Factor
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ABSTRACT: [reaction: see text] A highly regio- and stereoselective carbometalation reaction of fluoroalkylated internal alkynes with organocopper reagents is described. This reaction is utilized successfully in the short, stereoselective total synthesis of the antiestrogenic drug panomifene.
Organic Letters 04/2004; 6(6):933-6. · 5.86 Impact Factor
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ABSTRACT: The one-pot synthesis of trisubstituted alkenes starting from fluoroalkylated internal alkynes was investigated. Hydroboration of the alkynes proceeded in a highly regio- and stereoselective manner to give the corresponding vinylboranes in excellent yields. Without isolation, treatment of the vinylboranes with various aryl halides under the Suzuki-Miyaura cross-coupling conditions gave the fluoroalkylated trisubstituted alkenes in high yields with complete retention of the olefinic geometry.
Chemical Communications 04/2004; · 6.17 Impact Factor
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ABSTRACT: Carbostannylation of fluoroalkylated alkynes with various allylstannanes in the presence of AIBN was investigated. In the case of the allylstannane having an electron-withdrawing group at the beta position, the reaction proceeded highly regio- and stereoselectively to give the corresponding allylstannylated products in high yields. Even in the absence of AIBN, the reaction took place smoothly in a highly regio- and stereoselective manner under an atmosphere of air. Thus-obtained vinylstannanes were subjected to the Migita-Kosugi-Stille coupling reaction conditions, affording the tetrasubstituted alkenes in excellent yields.
The Journal of Organic Chemistry 04/2004; 69(6):2188-90. · 4.45 Impact Factor
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Tetrahedron. 61(39):9391-9404.
