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Nickel-Catalyzed C(2)-H Arylation of Indoles with Aryl Chlorides under Neat Conditions
Dilip K Pandey1, Muniyappa Vijaykumar1, Benudhar Punji1
1Organometallic Synthesis and Catalysis Group, Chemical Engineering Division , Academy of Scientific and Innovative Research (AcSIR) , CSIR-National Chemical Laboratory (CSIR-NCL) , Dr. Homi Bhabha Road , Pune 411 008 , Maharashtra , India.
Abstract:
Nickel-catalyzed regioselective C(2)-H arylation of indoles and pyrroles with aryl chlorides is achieved under neat conditions. This method allows the efficient coupling of diverse aryl chlorides employing a user-friendly and inexpensive Ni(OAc)2/dppf catalyst system at 80 °C. Numerous functionalities, such as halides, alkyl ether, fluoro-alkyl ether, and thioether, and substituted amines, including heteroarenes like benzothiazolyl, pyrrolyl, indolyl, and carbazolyl, are well tolerated under the reaction conditions. The preliminary mechanistic study highlights a single-electron transfer (SET) pathway for the arylation reaction.
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