Literature DB >> 16408981

Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex.

Oscar Navarro1, Nicolas Marion, Yoshihiro Oonishi, Roy A Kelly, Steven P Nolan.   

Abstract

[reaction: see text] The activity of the complex (IPr)PdCl(eta2-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for alpha-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.

Entities:  

Year:  2006        PMID: 16408981     DOI: 10.1021/jo0521201

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  13 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors:  Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Palladium-Catalyzed β-Arylation of α-Keto Esters.

Authors:  Blane P Zavesky; Samuel L Bartlett; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-04-11       Impact factor: 6.005

4.  Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

Authors:  Mark R Biscoe; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

5.  1-(4-tert-Butyl-benz-yl)-3-(3,4,5-tri-methoxy-benz-yl)benzimidazolium bromide monohydrate.

Authors:  Hakan Arslan; Don Vanderveer; Serpil Demir; Ismail Ozdemir; Bekir Cetinkaya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-24

6.  1-(1H-Benzimidazol-1-ylmeth-yl)-3-[2-(di-isopropyl-amino)eth-yl]-1H-benzimid-azolium bromide 0.25-hydrate.

Authors:  Hakan Arslan; Don Vanderveer; Serpil Demir; Ismail Ozdemir; Bekir Cetinkaya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-06

7.  Bromido[1-(η-4-tert-butyl-benz-yl)-3-(2,4,6-trimethyl-benz-yl)benzimidazol-2-yl-idene]chloridoruthenium(II).

Authors:  Hakan Arslan; Don Vanderveer; Ismail Ozdemir; Serpil Demir; Bekir Cetinkaya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-20

8.  1,3-Bis(thio-phen-2-ylmeth-yl)-3,4,5,6-tetra-hydro-pyrimidinium trichlorido(η-p-cymene)ruthenate(II).

Authors:  Hakan Arslan; Don Vanderveer; Ismail Ozdemir; Nevin Gürbüz; Yetkin Gök; Bekir Cetinkaya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-20

9.  Dichlorido[1-(2-methyl-benz-yl)-3-(η-2,4,6-trimethyl-benz-yl)-1H-2,3-dihydro-benzimidazol-2-yl-idene]ruthenium(II) dichloro-methane solvate.

Authors:  Hakan Arslan; Don Vanderveer; Sedat Yaşar; Ismail Ozdemir; Bekir Cetinkaya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-02-04

10.  1,3-Bis[4-(meth-oxy-carbon-yl)benz-yl]benzimidazolium bromide monohydrate.

Authors:  Hua-Rong Huang; Guo Wen-Jiao; Zhi-Yun Du; Yan-Xiong Fang; Kun Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-06
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