Literature DB >> 25711163

Nickel-catalyzed amination of aryl chlorides with ammonia or ammonium salts.

Rebecca A Green1, John F Hartwig.   

Abstract

The nickel-catalyzed amination of n class="Chemical">aryl chlorides to form primary arylamines occurs with ammonia or ammonium sulfate and a well-defined single-component nickel(0) precatalyst containing a Josiphos ligand and an η(2)-bound benzonitrile ligand. This system also catalyzes the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; ammonia; arylation; cross-coupling; nickel

Mesh:

Substances:

Year:  2015        PMID: 25711163      PMCID: PMC4480680          DOI: 10.1002/anie.201500404

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


  24 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.  Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions.

Authors:  Shaozhong Ge; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

3.  Nickel-catalyzed amination of aryl sulfamates.

Authors:  Stephen D Ramgren; Amanda L Silberstein; Yang Yang; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-20       Impact factor: 15.336

4.  An examination of the palladium/Mor-DalPhos catalyst system in the context of selective ammonia monoarylation at room temperature.

Authors:  Pamela G Alsabeh; Rylan J Lundgren; Robert McDonald; Carin C C Johansson Seechurn; Thomas J Colacot; Mark Stradiotto
Journal:  Chemistry       Date:  2013-01-04       Impact factor: 5.236

5.  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

6.  Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates.

Authors:  Nathaniel H Park; Georgiy Teverovskiy; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-11-27       Impact factor: 6.005

7.  BippyPhos: a single ligand with unprecedented scope in the Buchwald-Hartwig amination of (hetero)aryl chlorides.

Authors:  Sarah M Crawford; Christopher B Lavery; Mark Stradiotto
Journal:  Chemistry       Date:  2013-11-04       Impact factor: 5.236

8.  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

9.  Nickel-catalyzed amination of aryl tosylates.

Authors:  Cai-Yan Gao; Lian-Ming Yang
Journal:  J Org Chem       Date:  2008-01-17       Impact factor: 4.354

10.  Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation.

Authors:  Nathan D Schley; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

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  12 in total

1.  P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.

Authors:  Gen Li; Ziyang Qin; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2020-09-11       Impact factor: 15.419

2.  C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes.

Authors:  Chern-Hooi Lim; Max Kudisch; Bin Liu; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-06-11       Impact factor: 15.419

3.  Using JPP to Identify Ni Bidentate Phosphine Complexes In Situ.

Authors:  Matthew D Hannigan; Anne J McNeil; Paul M Zimmerman
Journal:  Inorg Chem       Date:  2021-08-18       Impact factor: 5.165

4.  Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light.

Authors:  Clarice A D Caiuby; Akbar Ali; Vinicius T Santana; Francisco W de S Lucas; Marilia S Santos; Arlene G Corrêa; Otaciro R Nascimento; Hao Jiang; Márcio W Paixão
Journal:  RSC Adv       Date:  2018-04-05       Impact factor: 4.036

5.  Ni-Catalyzed Enantioselective C-Acylation of α-Substituted Lactams.

Authors:  Masaki Hayashi; Shoshana Bachman; Satoshi Hashimoto; Chad C Eichman; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-07-15       Impact factor: 15.419

6.  Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C-H Activation.

Authors:  Erik Weis; Magnus J Johansson; Belén Martín-Matute
Journal:  Chemistry       Date:  2021-11-17       Impact factor: 5.020

7.  Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp3)-H bonds.

Authors:  José A Fernández-Salas; Enrico Marelli; Steven P Nolan
Journal:  Chem Sci       Date:  2015-06-22       Impact factor: 9.825

8.  Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).

Authors:  Ilja Rodstein; Daniel Sowa Prendes; Leon Wickert; Maurice Paaßen; Viktoria H Gessner
Journal:  J Org Chem       Date:  2020-09-21       Impact factor: 4.354

9.  Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design.

Authors:  Christopher M Lavoie; Preston M MacQueen; Nicolas L Rotta-Loria; Ryan S Sawatzky; Andrey Borzenko; Alicia J Chisholm; Breanna K V Hargreaves; Robert McDonald; Michael J Ferguson; Mark Stradiotto
Journal:  Nat Commun       Date:  2016-03-23       Impact factor: 14.919

10.  Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid.

Authors:  Silvia Roscales; Aurelio G Csákÿ
Journal:  ACS Omega       Date:  2019-08-12
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