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Sunday 6 March 2016

Pd(II) pincer type complex catalyzed tandem C-H and N-H activation of acetanilide in aqueous media: a concise access to functionalized carbazoles in a single step

 

 
Green Chem., 2016, Advance Article
DOI: 10.1039/C5GC02937F, Paper
Vignesh Arumugam, Werner Kaminsky, Dharmaraj Nallasamy
NNO Pincer type Pd(II) complex catalyzed one-pot synthesis of N-acetylcarbazoles in aqueous media is presented.

One-pot, tandem C–H and N–H activation of acetanilides with aryl boronic acids to realize functionalized carbazoles was conveniently performed under aerobic conditions using a novelNNO pincer type Pd(II) complex [Pd(L)Cl] (where L = nicotinic acid (phenyl-pyridin-2-yl-methylene)-hydrazide or furan-2-carboxylic acid (phenyl-pyridin-2-yl-methylene)-hydrazide) as a catalyst in neat water and a very low (0.01 mol%) amount of catalyst. It is worth noting that recyclability up to six consecutive runs and column chromatography free isolation of the title heterocycles in an excellent yield are achieved.
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Pd(II) pincer type complex catalyzed tandem C–H and N–H activation of acetanilide in aqueous media: a concise access to functionalized carbazoles in a single step

*Corresponding authors
aInorganic & Nanomaterials Research Laboratory, Department of Chemistry, Bharathiar University, Coimbatore 641 046, India
E-mail: dharmaraj@buc.edu.in
Web: http://ndharmaraj.wix.com/inrl
Fax: +91 4222422387
Tel: +91 4222428316
bDepartment of Chemistry, University of Washington, Seattle, USA
Green Chem., 2016, Advance Article
DOI: 10.1039/C5GC02937F
One-pot, tandem C–H and N–H activation of acetanilides with aryl boronic acids to realize functionalized carbazoles was conveniently performed under aerobic conditions using a novelNNO pincer type Pd(II) complex [Pd(L)Cl] (where L = nicotinic acid (phenyl-pyridin-2-yl-methylene)-hydrazide or furan-2-carboxylic acid (phenyl-pyridin-2-yl-methylene)-hydrazide) as a catalyst in neat water and a very low (0.01 mol%) amount of catalyst. It is worth noting that recyclability up to six consecutive runs and column chromatography free isolation of the title heterocycles in an excellent yield are achieved.
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