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

 

 

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.

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C5GC02937F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

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.

 

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

Vignesh Arumugam,^a   Werner Kaminsky^b and  Dharmaraj Nallasamy*^a  

 

 

*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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