Microwave Assisted Suzuki-Miyaura and Ullmann Type Homocoupling Reactions of 2- and 3-Halopyridines Using a Pd(OAc) 2 /Benzimidazolium Salt and Base Catalyst System

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Abstract

A number of novel benzimidazole derivatives 1– 4 were synthesized and the catalytic activity of these compounds in a catalytic system consisting of a benzimidazolium salt/Pd(OAc) ₂/K ₂CO ₃ were investigated in the Suzuki-Miyaura and Ullmann type homocoupling reactions under microwave irradiation. We obtained both cross coupling and homocoupling products of pyridine and some side products such as dimethylaminopyridine and unsubstituted pyridine.

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N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union.

George Fortman, Garry Nolan (2011)

Cross-coupling reactions using Pd-NHC (NHC = N-heterocyclic carbene) catalysts are discussed in this critical review and examined in terms of catalytic activity and how these have permitted advances in the area as they developed (95 references). This journal is © The Royal Society of Chemistry 2011

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Record: found
Abstract: found
Article: not found

Cross-coupling in flow.

Stephen Buchwald, Jason Noel (2011)

Until recently, cross-coupling reactions have been exclusively performed in batch processes. With the advent of microfluidics, significant effort has been devoted to develop a wide variety of continuous-flow techniques to facilitate organic synthesis. In this critical review, we attempt to give an overview of the different continuous-flow methodologies that have been developed and utilized for cross-coupling reactions. In addition, we attempt to point out the advantages of continuous-flow when compared with their batch counterparts (246 references). This journal is © The Royal Society of Chemistry 2011

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Record: found
Abstract: found
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Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates.

John Wolfe, Hiroshi Tomori, Joseph P Sadighi … (2000)

Palladium complexes supported by (o-biphenyl)P(t-Bu)(2) (3) or (o-biphenyl)PCy(2) (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 degrees C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.

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Author and article information

Journal

Journal ID (nlm-ta): Molecules

Journal ID (iso-abbrev): Molecules

Journal ID (publisher-id): molecules

Title: Molecules

Publisher: MDPI

ISSN (Electronic): 1420-3049

Publication date (Electronic): 25 March 2013

Publication date Collection: April 2013

Volume: 18

Issue: 4

Pages: 3712-3724

Affiliations

[1 ]Battalgazi Vocational School, İnönü University, Battalgazi, Malatya 44210, Turkey; E-Mail: ulku.yilmaz@ 123456inonu.edu.tr

[2 ]Department of Elementary Education, Faculty of Education, Hakkari University, Hakkari 30000, Turkey; E-Mail: selmadeniz@ 123456hakkari.edu.tr

[3 ]Department of Chemistry, Faculty of Science, İnönü University, Malatya 44280, Turkey

[4 ]Department of Elementary Education, Faculty of Education, Adıyaman University, Adıyaman 02040, Turkey; E-Mail: nsireci@ 123456adiyaman.edu.tr

Author notes

[* ] Author to whom correspondence should be addressed; E-Mail: hkucukbay@ 123456inonu.edu.tr ; Tel.: +90-422-377-3881; Fax: +90-422-341-0037.

Article

Publisher ID: molecules-18-03712

DOI: 10.3390/molecules18043712

PMC ID: 6269664

PubMed ID: 23529031

SO-VID: 87c68a51-40bc-403d-a1ae-be9d7b6ca55b

License:

This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

History

Date received : 01 March 2013

Date revision received : 15 March 2013

Date accepted : 15 March 2013

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