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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
[4 + 2] Annulation of CF3-π-Allyl-Pd Species with Isatic Acids for Direct Access to 3-Trifluoroethyl-4-carboxylate
Rami Sateesh1,2, Chiliveru Priyanka1,2, Krishna Swaroop Desireddy1,2
1Fluoro-Agro Chemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
Herein, we report a catalytic [4 + 2] annulation between trifluoromethyl allyl carbonates and isatic acids that provides direct access to 3-trifluoroethyl-4-carboxylate quinolines. The transformation proceeds smoothly under mild conditions and accommodates a broad range of electron-donating, electron-withdrawing, and sterically demanding substituents. In addition, a one-pot protocol enables efficient conversion of the annulation products into 3-trifluoroethyl-4-amido quinolines under the same reaction conditions. The synthetic versatility of this strategy is further demonstrated through the one-pot preparation of a trifluoroethyl analogue of brequinar, as well as the streamlined synthesis of trifluoroethylated analogues of bioactive scaffolds.
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