Issue 34, 2016

Rh(iii)-catalyzed relay carbenoid functionalization of aromatic C–H bonds: access to π-conjugated fused heteroarenes

Abstract

A novel Rh(III)-catalyzed relay cross-coupling/cyclization cascade between arylketoimines and diazoesters is described. This transformation provides a concise access to unique π-conjugated 1-azaphenalenes (1-APLEs) via a double aryl Csp2–H bond carbenoid functionalization process. As illustrative examples, the 1-APLE-based π-conjugated molecules which possess low-lying HOMO levels could be converted to promising organic optoelectronic materials.

Graphical abstract: Rh(iii)-catalyzed relay carbenoid functionalization of aromatic C–H bonds: access to π-conjugated fused heteroarenes

Supplementary files

Article information

Article type
Communication
Submitted
11 Jan 2016
Accepted
29 Mar 2016
First published
29 Mar 2016

Chem. Commun., 2016,52, 5856-5859

Author version available

Rh(III)-catalyzed relay carbenoid functionalization of aromatic C–H bonds: access to π-conjugated fused heteroarenes

Y. Xie, X. Chen, X. Liu, S. Su, J. Li and W. Zeng, Chem. Commun., 2016, 52, 5856 DOI: 10.1039/C6CC00254D

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