Palladium catalysed regioselective arylation of indoles, benzofuran and benzothiophene with aryldiazonium salts

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Efficient palladium-catalyzed N-arylation of indoles.

[equation--see text] The N-arylation of indoles, including a variety of substituted ones, has been carried out using bulky, electron-rich phosphines as the supporting ligand in combination with Pd(2)(dba)(3). Using this catalyst system, the efficient coupling of indole and a variety of substituted indoles with aryl iodides, bromides, chlorides, and triflates can be achieved.

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A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 °C.

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The carbamate (-O2CNR2) function is an excellent directing group for palladium-catalysed direct arylation reactions giving both protected or free mono- or di-substituted phenols, as well as an example of a dibenzopyranone, depending on coupling partners (aryl iodides or diaryliodonium salts) and conditions.

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ژورنال

عنوان ژورنال: RSC Advances

سال: 2012

ISSN: 2046-2069

DOI: 10.1039/c2ra22213b