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Divergent Syntheses of Indoles and Quinolines Involving N1-C2-C3 Bond Formation through Two Distinct Pd Catalyses

Su San Jang, Young Ho Kim and So Won Youn*

*Center for New Directions in Organic Synthesis, Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 04763, Korea, Email: sowony73hanyang.ac.kr

S. S. Jang, Y. H. Kim, S. W. Youn, Org. Lett., 2020, 22, 9151-9157.

DOI: 10.1021/acs.orglett.0c02898 (free Supporting Information)



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Abstract

Pd-catalyzed annulative couplings of 2-alkenylanilines with aldehydes using alcohols as both the solvent and hydrogen source allow divergent syntheses of indoles and quinolines via two distinct mechanisms by simply tuning reaction parameters. Whereas a reaction using Xantphos as ligand in EtOH provides indoles, a reaction with DPEphos in 2,2,2-trifluoroethanol provides quinolines.

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Key Words

indoles


ID: J54-Y2020