Abstract
A selective and efficient method for the synthesis of 3-aryl-2-(methylthio)benzo[ b]furans derivatives by palladium catalyzed cross-coupling reaction with boronic acids has been developed. The reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron donating and neutral substituents.
Highlights
The construction of benzo[b]furans substituted in the 2,3 positions is of great synthetic interest due to the presence of this moiety in many complex compounds, which have potential therapeutic applications.[1]
The palladium-catalyzed Suzuki cross-coupling reaction of aryl halides with organoboron reagents has become a common and convenient synthetic method in organic chemistry.[3]
Our initial studies on Suzuki cross-coupling focused on the development of an optimum set of reaction conditions
Summary
The construction of benzo[b]furans substituted in the 2,3 positions is of great synthetic interest due to the presence of this moiety in many complex compounds, which have potential therapeutic applications.[1]. Since the Suzuki reaction has proven to be successful for the selective arylation of heterocyles,[2] it was of interest to explore this reaction to obtain 3-aryl-2-(methylthio) benzo[b]furan derivatives. To our knowledge this methodology has not been explored and we wish to report the application of 3-iodo-2-(methylthio)benzo[b] furans 1a-c as substrates on the cross-coupling reaction with boronic acids 2a-k in the presence of a palladium salt to obtain 3-aryl-2-(methylthio)benzo[b]furans 3a-u (Scheme 1). Palladium Catalyzed Suzuki Cross-Coupling of 3-Iodo-2-(methylthio)-benzo[b]furan Derivatives.
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