Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes?

Chemical Science Pub Date: 2013-01-18 DOI: 10.1039/C3SC22241A

Abstract

The chelation-assisted strategy has been endowed with some novel functions in the Rh(III)-catalyzed dehydrogenative coupling of indoles/pyrroles with heteroarenes. While the reaction conditions used are rather common, the strategy can close the homo-coupling pathway of each coupling partner, and dramatically extend substrate scope along with the exclusive indole or pyrrole C2-site selectivity. This is the first example describing that a catalytic system allows the oxidative C–H/C–H hetero-coupling not only between two electron-rich heteroarenes but also between electron-deficient and electron-rich heteroarenes, showing a further beneficial aspect of the Rh(III) catalysis.

Graphical abstract: Chelation-assisted Rh(iii)-catalyzed C2-selective oxidative C–H/C–H cross-coupling of indoles/pyrroles with heteroarenes
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