Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium-Catalyzed Enantioselective C(sp3)–H Functionalization

Authors


  • This work is supported by the EPFL, the ETH Zurich (ETH-16 08-3), and by the European Research Council under the European Community’s Seventh Framework Program (FP7 2007-2013)/ERC Grant agreement no 257891. We thank Dr. R. Scopelliti for X-ray crystallographic analysis of 9 a and Dr. R. Kadyrov (Evonik Industries AG) for generous donations of 2,5-dimethyl-1-TMS-phospholane.

Abstract

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Teaming up: The important indoline scaffold is provided with enantiomeric ratios of up to 98:2 in palladium(0)-catalyzed C(sp3)–H activations of aryl triflates. The key is the combination of the electron-rich monodentate Sagephos and the bulky 9H-xanthene-9-carboxylic acid. Both participate in a highly cooperative manner in the enantiodetermining concerted-deprotonation-metalation step (see scheme, Tf=triflate).

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