The conversion of phenols to the corresponding aryl halides under mild conditions
Mild, novel procedures have been developed for the syntheses of aryl halides from the corresponding phenols in modest to good yields via boronate ester intermediates.
Thompson, Alicia L. S.,Kabalka, George W.,Akula, Murthy R.,Huffman, John W.
p. 547 - 550
(2007/10/03)
Preparation and Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Triflates
Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups. Several examples of di-ortho-substituted triflates are successfully coupled with these reagents.
Seganish, W. Michael,DeShong, Philip
p. 1137 - 1143
(2007/10/03)
Deoxygenation of Highly Hindered Phenols
Highly hindered phenolic compounds can be efficiently deoxygenated by reduction of the corresponding triflates under homogeneous or heterogeneous (Pd/C) conditions.Reductive deoxygenation under homogeneous conditions has been shown to occur both in the presence of acid (HCOOH, CH3COOH, (CH3)3CCOOH, PhCH2COOH) or in its absence.The concomitant formation of dibutylformamide apparently derives from aminolysis of DMF by dibutylamine, the Pd(0)-catalyzed hydrolysis product of tributylamine.Deuteration experiments suggest that several hydrogen (or deuterium) sources operate in the hydrogenolysis processes studied.
Saa, Jose M.,Dopico, Mercedes,Martorell, Gabriel,Garcia-Raso, Angel
p. 991 - 995
(2007/10/02)
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