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Literature DB >> 25711163

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

Abstract

The nickel-catalyzed amination of 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.

Entities: Chemical Gene

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

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 J_PP 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