Pd-catalyzed 5- cyclization/etherification cascade of -propargyl arylamines for the synthesis of polysubstituted furans.

Chem Commun (Camb)

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

Published: July 2024

A method for the synthesis of furans bearing indoline skeletons was developed an intramolecular palladium-catalyzed 5- cyclization/etherification cascade of -propargyl arylamines containing a 1,3-dicarbonyl side chain. This method realized the first capture of vinyl carbopalladiums by ketones as -nucleophiles and showed a wide range of substrate tolerability affording trisubstituted furans in various yields. The enantioselective version for this domino process and diverse derivatizations of the reaction products were also studied.

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http://dx.doi.org/10.1039/d4cc02255fDOI Listing

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Pd-catalyzed 5- cyclization/etherification cascade of -propargyl arylamines for the synthesis of polysubstituted furans.

Chem Commun (Camb)

July 2024

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

A method for the synthesis of furans bearing indoline skeletons was developed an intramolecular palladium-catalyzed 5- cyclization/etherification cascade of -propargyl arylamines containing a 1,3-dicarbonyl side chain. This method realized the first capture of vinyl carbopalladiums by ketones as -nucleophiles and showed a wide range of substrate tolerability affording trisubstituted furans in various yields. The enantioselective version for this domino process and diverse derivatizations of the reaction products were also studied.

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