Literature DB >> 16209512

CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds.

Xiaoan Xie1, Guorong Cai, Dawei Ma.   

Abstract

[reaction: see text] The arylation of ethyl acetoacetate, ethyl benzoyl acetate, and diethyl malonate under the catalysis of CuI/L-proline in DMSO proceeds smoothly at 40-50 degrees C in the presence of Cs2CO3 to provide the 2-aryl-1,3-dicarbonyl compounds in good yields. Both aryl iodides and aryl bromides are compatible with these reaction conditions.

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Year:  2005        PMID: 16209512     DOI: 10.1021/ol0518838

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  12 in total

1.  Copper(I) enolate complexes in α-arylation reactions: synthesis, reactivity, and mechanism.

Authors:  Zheng Huang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-08       Impact factor: 15.336

2.  Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

Authors:  Laxmidhar Rout; Sridhar Regati; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-12-06       Impact factor: 5.837

3.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

4.  Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.

Authors:  Lingchao Cai; Kui Zhang; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2016-03-04       Impact factor: 15.419

5.  Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone.

Authors:  Liming Cao; John P Maciejewski; Stephan Elzner; David Amantini; Peter Wipf
Journal:  Org Biomol Chem       Date:  2012-04-04       Impact factor: 3.876

6.  Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.

Authors:  Andrii Monastyrskyi; Niranjan K Namelikonda; Roman Manetsch
Journal:  J Org Chem       Date:  2015-02-24       Impact factor: 4.354

7.  Synthesis of Imidazo[1,2-f]phenanthridines by Recyclable Magnetic MOF-Catalyzed Coupling and Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones Followed by Aromatization.

Authors:  Seong Weon Lee; Pham Duy Quang Dao; Ho-Jin Lim; Chan Sik Cho
Journal:  ACS Omega       Date:  2022-05-24

8.  Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols.

Authors:  Debabrata Maiti; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds.

Authors:  Daniel Best; David J Burns; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-08       Impact factor: 15.336

10.  A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline.

Authors:  Chunpu Li; Lei Zhang; Shuangjie Shu; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2014-10-21       Impact factor: 2.883

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