Issue 8, 2015

I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C–H functionalization

Abstract

One-pot, atom-economic synthesis of quinoxalines has been achieved through generation of arylglyoxal from easily available ethylarenes, ethylenearenes and ethynearenes, and subsequent condensation with o-phenylenediamines. Catalytic I2 with TBHP as an oxidant in DMSO is the system of choice for this domino reaction involving C–H functionalization/oxidative cyclization. This metal-free, mechanistically distinct and functional group tolerant tandem approach could be a powerful complement to traditional approaches for the synthesis of quinoxalines.

Graphical abstract: I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C–H functionalization

Supplementary files

Article information

Article type
Paper
Submitted
13 Aug 2014
Accepted
08 Dec 2014
First published
10 Dec 2014

RSC Adv., 2015,5, 5580-5590

Author version available

I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C–H functionalization

K. S. Vadagaonkar, H. P. Kalmode, K. Murugan and A. C. Chaskar, RSC Adv., 2015, 5, 5580 DOI: 10.1039/C4RA08589B

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