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Exceptionally Mild Palladium(II)-Catalyzed Dehydrogenative C–H/C–H Arylation of Indolines at the C‑7 Position under Air

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journal contribution
posted on 21.11.2014, 00:00 by Lin-Yu Jiao, Polina Smirnov, Martin Oestreich
An improved method for the dehydrogenative C–H/C–H cross-coupling at the C-7 position of indolines containing a urea as a directing group is reported. The new protocol is a rare example of an aerobic palladium­(II)-catalyzed cross dehydrogenative coupling (CDC) reaction that proceeds at low temperature. The use of either Cu­(OAc)2 in an open flask or dioxygen (balloon) at 50 °C tolerates indolines not substituted at C-2 and C-3, thereby extending the scope of the previous method that suffers from indoline-to-indole oxidation.