Literature DB >> 19122797

Regioselective Copper-catalyzed C-N and C-S Bond Formation using Amines, Thiols and Halobenzoic Acids.

Shuanglong Liu1, John Paul C Pestano, Christian Wolf.   

Abstract

A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu(2)O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81 to 99% yield.

Entities:  

Year:  2007        PMID： 19122797      PMCID： PMC2613345          DOI： 10.1055/s-2007-990875

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  25 in total

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2.  Synthesis, structure, and activity of diclofenac analogues as transthyretin amyloid fibril formation inhibitors.

Authors:  Vibha B Oza; Craig Smith; Prakash Raman; Edward K Koepf; Hilal A Lashuel; H Mike Petrassi; Kyle P Chiang; Evan T Powers; James Sachettinni; Jeffery W Kelly
Journal:  J Med Chem       Date:  2002-01-17       Impact factor: 7.446

3.  Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines.

Authors:  Christian Wolf; Shuanglong Liu; Xuefeng Mei; Adam T August; Michael D Casimir
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

4.  Regioselective copper-catalyzed amination of chlorobenzoic acids: synthesis and solid-state structures of N-aryl anthranilic acid derivatives.

Authors:  Xuefeng Mei; Adam T August; Christian Wolf
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

5.  Mechanism for the noncovalent chiral domino effect: new paradigm for the chiral role of the N-terminal segment in a 3(10)-helix.

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Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

6.  Synthesis of conformationally stable 1,8-diarylnaphthalenes: development of new photoluminescent sensors for ion-selective recognition.

Authors:  Christian Wolf; Xuefeng Mei
Journal:  J Am Chem Soc       Date:  2003-09-03       Impact factor: 15.419

7.  Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

Authors:  Xiaohua Huang; Kevin W Anderson; Danilo Zim; Lei Jiang; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-06-04       Impact factor: 15.419

8.  A highly congested N,N'-dioxide fluorosensor for enantioselective recognition of chiral hydrogen bond donors.

Authors:  Xuefeng Mei; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2004-08-10       Impact factor: 6.222

9.  A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.

Authors:  Manuel A Fernández-Rodríguez; Qilong Shen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

10.  Synthesis and characterization of potent bivalent amyloidosis inhibitors that bind prior to transthyretin tetramerization.

Authors:  Nora S Green; Satheesh K Palaninathan; James C Sacchettini; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2003-11-05       Impact factor: 15.419
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  2 in total

1.  Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas.

Authors:  Kekeli Ekoue-Kovi; Kimberly Yearick; Daniel P Iwaniuk; Jayakumar K Natarajan; John Alumasa; Angel C de Dios; Paul D Roepe; Christian Wolf
Journal:  Bioorg Med Chem       Date:  2008-11-12       Impact factor: 3.641

2.  Discovery of anthranilamides as a novel class of inhibitors of neurotropic alphavirus replication.

Authors:  Scott J Barraza; Philip C Delekta; Janice A Sindac; Craig J Dobry; Jianming Xiang; Richard F Keep; David J Miller; Scott D Larsen
Journal:  Bioorg Med Chem       Date:  2015-02-11       Impact factor: 3.641
  2 in total

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