Literature DB >> 18224651

Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Michael G Organ1, Mirvat Abdel-Hadi, Stephanie Avola, Igor Dubovyk, Niloufar Hadei, Eric Assen B Kantchev, Christopher J O'Brien, Mahmoud Sayah, Cory Valente.   

Abstract

Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination protocols mediated by Pd-PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides. Variations in solvent polarity, base and temperature are tolerated, enhancing the scope and utility of this protocol. A mechanistic rationalization for base strength (pKb) requirements is also provided.

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Year:  2008        PMID： 18224651     DOI： 10.1002/chem.200701621

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  14 in total

1.  Pd-catalyzed amination as an alternative to nucleophilic aromatic substitution for the synthesis of N-alkyltacrines and analogues.

Authors:  Ming Ma; Jimit Mehta; Larry D Williams; Paul R Carlier
Journal:  Tetrahedron Lett       Date:  2011-02-23       Impact factor: 2.415

2.  Design of New Ligands for the Palladium-Catalyzed Arylation of α-Branched Secondary Amines.

Authors:  Nathaniel H Park; Ekaterina V Vinogradova; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

3.  Pd-Catalyzed C-N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines.

Authors:  Joseph M Dennis; Nicholas A White; Richard Y Liu; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-03-15       Impact factor: 13.084

4.  Aminations of Aryl Bromides in Water at Room Temperature.

Authors:  Bruce H Lipshutz; David W Chung; Brian Rich
Journal:  Adv Synth Catal       Date:  2009-08       Impact factor: 5.837

5.  Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors:  Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-04-17       Impact factor: 4.354

6.  Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

Authors:  Sii Hong Lau; Peng Yu; Liye Chen; Christina B Madsen-Duggan; Michael J Williams; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2020-11-12       Impact factor: 15.419

7.  Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.

Authors:  Carolin Fischer; Burkhard Koenig
Journal:  Beilstein J Org Chem       Date:  2011-01-14       Impact factor: 2.883

8.  C(acyl)-C(sp2) and C(sp2)-C(sp2) Suzuki-Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes.

Authors:  Sinem Çakır; Serdar Batıkan Kavukcu; Hande Karabıyık; Senthil Rethinam; Hayati Türkmen
Journal:  RSC Adv       Date:  2021-11-23       Impact factor: 4.036

9.  Amination of heteroaryl chlorides: palladium catalysis or SN Ar in green solvents?

Authors:  Katie Walsh; Helen F Sneddon; Christopher J Moody
Journal:  ChemSusChem       Date:  2013-06-21       Impact factor: 8.928

10.  Rational ligand design for the arylation of hindered primary amines guided by reaction progress kinetic analysis.

Authors:  Paula Ruiz-Castillo; Donna G Blackmond; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-02-18       Impact factor: 15.419
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