Issue 5, 2013

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Dec 2012
Accepted
17 Jan 2013
First published
18 Jan 2013

Chem. Sci., 2013,4, 1964-1969

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

X. Qin, H. Liu, D. Qin, Q. Wu, J. You, D. Zhao, Q. Guo, X. Huang and J. Lan, Chem. Sci., 2013, 4, 1964 DOI: 10.1039/C3SC22241A

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