Literature DB >> 14602009

Ligand- and base-free copper(II)-catalyzed C-N bond formation: cross-coupling reactions of organoboron compounds with aliphatic amines and anilines.

Tan D Quach1, Robert A Batey.   

Abstract

[reaction: see text] A ligandless and base-free Cu-catalyzed protocol for the cross-coupling of arylboronic acids and potassium aryltrifluoroborate salts with primary and secondary aliphatic amines and anilines is described. The process utilizes catalytic copper(II) acetate monohydrate and 4 A molecular sieves in dichloromethane at slightly elevated temperatures under an atmosphere of oxygen. A broad range of functional groups are tolerated on both of the cross-coupling partners.

Entities:  

Year:  2003        PMID: 14602009     DOI: 10.1021/ol035681s

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


  12 in total

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2.  Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D.

Authors:  Elliot D Mock; Ioli Kotsogianni; Wouter P F Driever; Carmen S Fonseca; Jelle M Vooijs; Hans den Dulk; Constant A A van Boeckel; Mario van der Stelt
Journal:  J Med Chem       Date:  2020-12-31       Impact factor: 7.446

3.  Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines.

Authors:  Xinyu Guan; Haoran Zhu; Tom G Driver
Journal:  ACS Catal       Date:  2021-09-23       Impact factor: 13.700

4.  (18)F-click labeling of a bombesin antagonist with an alkyne-(18)F-ArBF(3) (-): in vivo PET imaging of tumors expressing the GRP-receptor.

Authors:  Ying Li; Zhibo Liu; Curtis W Harwig; Maral Pourghiasian; Joseph Lau; Kuo-Shyan Lin; Paul Schaffer; Francois Benard; David M Perrin
Journal:  Am J Nucl Med Mol Imaging       Date:  2013-01-05

5.  (1)H, (13)C, (19)F and (11)B NMR spectral reference data of some potassium organotrifluoroborates.

Authors:  Roberta A Oliveira; Ricardo O Silva; Gary A Molander; Paulo H Menezes
Journal:  Magn Reson Chem       Date:  2009-10       Impact factor: 2.447

6.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

7.  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a potent inhibitor of bacterial phosphopantetheinyl transferase that attenuates secondary metabolism and thwarts bacterial growth.

Authors:  Timothy L Foley; Ganesha Rai; Adam Yasgar; Thomas Daniel; Heather L Baker; Matias Attene-Ramos; Nicolas M Kosa; William Leister; Michael D Burkart; Ajit Jadhav; Anton Simeonov; David J Maloney
Journal:  J Med Chem       Date:  2014-01-22       Impact factor: 7.446

8.  Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.

Authors:  Emilien Demory; Karthik Devaraj; Andreas Orthaber; Paul J Gates; Lukasz T Pilarski
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-13       Impact factor: 15.336

9.  New efficient ligand for sub-mol % copper-catalyzed C-N cross-coupling reactions running under air.

Authors:  Per-Fredrik Larsson; Peter Astvik; Per-Ola Norrby
Journal:  Beilstein J Org Chem       Date:  2012-11-09       Impact factor: 2.883

10.  Synthesis of Arylamines via Aminium Radicals.

Authors:  Thomas D Svejstrup; Alessandro Ruffoni; Fabio Juliá; Valentin M Aubert; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

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