Copper catalyzed coupling of aryl chlorides, bromides and iodides with amines and amides.

Chem Commun (Camb)

Department of Chemistry, Georgetown University, Washington, DC 20057, USA.

Published: April 2009

A copper(I) catalyzed procedure for carbon-nitrogen bond formation utilizing aryl halides and either amines, including amino acids and diphenylamine, or aliphatic and aromatic amides is described.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b823407hDOI Listing

Publication Analysis

Top Keywords

copper catalyzed
4
catalyzed coupling
4
coupling aryl
4
aryl chlorides
4
chlorides bromides
4
bromides iodides
4
iodides amines
4
amines amides
4
amides copperi
4
copperi catalyzed
4

Similar Publications

Copper(II)-Catalyzed Asymmetric (3+3) Annulation of Diaziridines with Oxiranes.

Org Lett

January 2025

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

Highly asymmetric (3+3) annulation of diaziridines with oxiranes via C-N bond cleavage in diaziridine was achieved under 10 mol % of chiral copper(II) complex as the catalyst under mild reaction conditions. With Cu(OTf) as the Lewis acid and C-symmetric imidazolidine-pyrroloimidazolone pyridine as the ligand, diverse tetrahydro-[1,3,4]-oxadiazines were obtained by stereospecific C-N/C-O bond formation in moderate to good yields (up to 93% yield) and high diastereo- (>20:1 dr) and enantioselectivities (up to 92% ee). The catalytic cycle and stereochemical model were proposed by DFT calculation.

View Article and Find Full Text PDF

Over the past decade, dioxazolones have been widely used as -acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among the 3d transition metals, copper catalysts have been gaining increasing attention owing to their abundance, cost-effectiveness, and sustainability.

View Article and Find Full Text PDF

Peptide Crosslinking by a Class of Plant Copper Enzymes.

Trends Chem

November 2024

Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC 27402, United States.

BURP domain peptide cyclases, or BpCs (an abbreviation we recommend in this opinion), are an emerging class of copper enzymes which catalyze the oxidative macrocyclization of peptides in plants. A close examination of their novel protein fold, along with the unique dicopper active site that meticulously controls crosslinking within peptides, highlights how nature exploits intricate mechanistic strategies to achieve diverse functionalities. Here, we summarize recent discoveries regarding the sequence, structure, function, and proposed chemistry of BpCs.

View Article and Find Full Text PDF

Enantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.

Angew Chem Int Ed Engl

January 2025

University of Toronto, Dept. of Chemistry, 80 St. George Street, M5S 3H6, Toronto, CANADA.

A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.

View Article and Find Full Text PDF

The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C-C bond activation via oxidative addition of transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters and MCPs to produce α-allylated 2-pyrrole derivatives. In this reaction, azomethine ylide formed by a chiral copper catalyst with ketimine ester would serve as a nucleophile to react with activated MCPs via palladium catalysis.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!