Literature DB >> 19260648

Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

Sirilata Yotphan1, Robert G Bergman, Jonathan A Ellman.   

Abstract

A method for the direct arylation of benzotriazepines is reported, employing an aryl iodide as the coupling partner, copper iodide as the catalyst, and lithium tert-butoxide as the base. A variety of electron-rich, electron-poor, and sterically hindered aryl iodides are compatible with the reaction conditions. The arylation reaction can also be performed outside a glovebox in air without a significant decrease in yield. Furthermore, convenient microwave conditions for carrying out this transformation are reported.

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Year:  2009        PMID： 19260648      PMCID： PMC2674648          DOI： 10.1021/ol900103a

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


  16 in total

Review 1.  Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors:  Dino Alberico; Mark E Scott; Mark Lautens
Journal:  Chem Rev       Date:  2007-01       Impact factor: 60.622

Review 2.  Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2007-03-05       Impact factor: 54.564

3.  Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2008-01-09       Impact factor: 15.419

4.  New synthesis of 1,3-dihydro-1,4-benzodiazepin-2(2H)-ones and 3-amino-1,3-dihydro-1,4-benzodiazepin-2(2H)-ones: Pd-catalyzed cross-coupling of imidoyl chlorides with organoboronic acids.

Authors:  Alan Nadin; José M Sánchez López; Andrew P Owens; Dean M Howells; Adam C Talbot; Timothy Harrison
Journal:  J Org Chem       Date:  2003-04-04       Impact factor: 4.354

5.  Thiazolothiazepine inhibitors of HIV-1 integrase.

Authors:  N Neamati; J A Turpin; H E Winslow; J L Christensen; K Williamson; A Orr; W G Rice; Y Pommier; A Garofalo; A Brizzi; G Campiani; I Fiorini; V Nacci
Journal:  J Med Chem       Date:  1999-08-26       Impact factor: 7.446

6.  Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules.

Authors:  Louis-Charles Campeau; Keith Fagnou
Journal:  Chem Commun (Camb)       Date:  2006-01-30       Impact factor: 6.222

7.  Discovery and characterization of novel, potent, non-peptide parathyroid hormone-1 receptor antagonists.

Authors:  Iain M McDonald; Carol Austin; Ildiko M Buck; David J Dunstone; John Gaffen; Eric Griffin; Elaine A Harper; Robert A D Hull; S Barret Kalindjian; Ian D Linney; Caroline M R Low; Dipa Patel; Michael J Pether; Michelle Raynor; Sonia P Roberts; Mark E Shaxted; John Spencer; Katherine I M Steel; David A Sykes; Paul T Wright; Wei Xun
Journal:  J Med Chem       Date:  2007-09-12       Impact factor: 7.446

Review 8.  Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation.

Authors:  Jared C Lewis; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2008-07-11       Impact factor: 22.384

9.  Optimization of 1,3,4-benzotriazepine-based CCK(2) antagonists to obtain potent, orally active inhibitors of gastrin-mediated gastric acid secretion.

Authors:  Iain M McDonald; James W Black; Ildiko M Buck; David J Dunstone; Eric P Griffin; Elaine A Harper; Robert A D Hull; S Barret Kalindjian; Elliot J Lilley; Ian D Linney; Michael J Pether; Sonia P Roberts; Mark E Shaxted; John Spencer; Katherine I M Steel; David A Sykes; Martin K Walker; Gillian F Watt; Laurence Wright; Paul T Wright; Wei Xun
Journal:  J Med Chem       Date:  2007-05-31       Impact factor: 7.446

10.  Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes.

Authors:  François Besselièvre; Sandrine Piguel; Florence Mahuteau-Betzer; David S Grierson
Journal:  Org Lett       Date:  2008-08-23       Impact factor: 6.005
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  9 in total

1.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

2.  A general method for copper-catalyzed arene cross-dimerization.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-08-08       Impact factor: 15.419

3.  Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

4.  Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.

Authors:  Thanh Truong; Joseph Alvarado; Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

5.  Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates.

Authors:  Thanh Truong; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2011-03-08       Impact factor: 15.419

6.  Iron-catalyzed heterocycle and arene deprotonative alkylation.

Authors:  Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

7.  Copper-catalyzed arene C-H bond cross-coupling.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2009-09-28       Impact factor: 6.222

8.  An aromatic Glaser-Hay reaction.

Authors:  Hien-Quang Do; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

9.  Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles.

Authors:  Rajkumar Jeyachandran; Harish Kumar Potukuchi; Lutz Ackermann
Journal:  Beilstein J Org Chem       Date:  2012-10-16       Impact factor: 2.883
  9 in total

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