Literature DB >> 20857466

Catalytic organometallic reactions of ammonia.

Jessica L Klinkenberg1, John F Hartwig.   

Abstract

Until recently, ammonia had rarely succumbed to catalytic transformations with homogeneous catalysts, and the development of such reactions that are selective for the formation of single products under mild conditions has encountered numerous challenges. However, recently developed catalysts have allowed several classes of reactions to create products with nitrogen-containing functional groups from ammonia. These reactions include hydroaminomethylation, reductive amination, alkylation, allylic substitution, hydroamination, and cross-coupling. This Minireview describes examples of these processes and the factors that control catalyst activity and selectivity.

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Year:  2011        PMID: 20857466      PMCID: PMC3261073          DOI: 10.1002/anie.201002354

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  29 in total

1.  Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines.

Authors:  David S Surry; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-08-02       Impact factor: 15.419

2.  Homogeneous catalytic hydroamination of alkynes and allenes with ammonia.

Authors:  Vincent Lavallo; Guido D Frey; Bruno Donnadieu; Michele Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  A very simple copper-catalyzed synthesis of anilines by employing aqueous ammonia.

Authors:  Ning Xia; Marc Taillefer
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Cleavage of X-H bonds (X = N, o, or C) by copper(I) alkyl complexes to form monomeric two-coordinate copper(I) systems.

Authors:  Laurel A Goj; Elizabeth D Blue; Colleen Munro-Leighton; T Brent Gunnoe; Jeffrey L Petersen
Journal:  Inorg Chem       Date:  2005-11-28       Impact factor: 5.165

5.  Salt-free iridium-catalyzed asymmetric allylic aminations with N,N-diacylamines and ortho-nosylamide as ammonia equivalents.

Authors:  Robert Weihofen; Olena Tverskoy; Günter Helmchen
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

6.  Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems.

Authors:  G A Grasa; M S Viciu; J Huang; S P Nolan
Journal:  J Org Chem       Date:  2001-11-16       Impact factor: 4.354

7.  Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines.

Authors:  Giang D Vo; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

8.  Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil.

Authors:  Cédric Bouteiller; Javier Becerril-Ortega; Patrice Marchand; Olivier Nicole; Louisa Barré; Alain Buisson; Cécile Perrio
Journal:  Org Biomol Chem       Date:  2010-01-06       Impact factor: 3.876

9.  Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature.

Authors:  Jinho Kim; Sukbok Chang
Journal:  Chem Commun (Camb)       Date:  2008-05-23       Impact factor: 6.222

10.  N-trialkylsilylimines as coupling partners for pd-catalyzed C[bond]N-forming reactions: one-step synthesis of imines and azadienes from aryl and alkenyl bromides.

Authors:  José Barluenga; Fernando Aznar; Carlos Valdés
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-03       Impact factor: 15.336

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  21 in total

1.  NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors:  Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2017-07-03       Impact factor: 15.419

2.  A Brief Survey of our Contribution to Stable Carbene Chemistry.

Authors:  David Martin; Mohand Melaimi; Michele Soleilhavoup; Guy Bertrand
Journal:  Organometallics       Date:  2011-09-22       Impact factor: 3.876

3.  Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds.

Authors:  Hongyin Gao; Zhe Zhou; Doo-Hyun Kwon; James Coombs; Steven Jones; Nicole Erin Behnke; Daniel H Ess; László Kürti
Journal:  Nat Chem       Date:  2016-11-28       Impact factor: 24.427

4.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

Review 5.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

6.  Elusive metal-free primary amination of arylboronic acids: synthetic studies and mechanism by density functional theory.

Authors:  Chen Zhu; Gongqiang Li; Daniel H Ess; John R Falck; László Kürti
Journal:  J Am Chem Soc       Date:  2012-10-25       Impact factor: 15.419

7.  How bulky ligands control the chemoselectivity of Pd-catalyzed N-arylation of ammonia.

Authors:  Seoung-Tae Kim; Suyeon Kim; Mu-Hyun Baik
Journal:  Chem Sci       Date:  2019-12-12       Impact factor: 9.825

8.  Mechanistic Studies of Palladium-Catalyzed Aminocarbonylation of Aryl Chlorides with Carbon Monoxide and Ammonia.

Authors:  Justin Y Wang; Alexandra E Strom; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-06-18       Impact factor: 16.383

9.  Palladium-catalyzed amination of aryl chlorides and bromides with ammonium salts.

Authors:  Rebecca A Green; John F Hartwig
Journal:  Org Lett       Date:  2014-08-18       Impact factor: 6.005

10.  From racemic alcohols to enantiopure amines: Ru-catalyzed diastereoselective amination.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  J Am Chem Soc       Date:  2014-08-29       Impact factor: 15.419

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