The complementary competitors: palladium and copper in C–N cross-coupling reactions

IP Beletskaya, AV Cheprakov - Organometallics, 2012 - ACS Publications
The C–N cross-coupling chemistry intensely developed since the late 1990s has supplied
synthesists with an overwhelming number of methods to effectively combine carbon and …

Bayesian optimization as a sustainable strategy for early-stage process development? A case study of Cu-catalyzed C–N coupling of sterically hindered pyrazines

E Braconi, E Godineau - ACS Sustainable Chemistry & …, 2023 - ACS Publications
Bayesian optimization is a powerful machine learning technique that is particularly well-
suited for optimizing chemical reactions in the early stages of process development. It can …

Efficient ruthenium-catalyzed N-methylation of amines using methanol

TT Dang, B Ramalingam, AM Seayad - ACS Catalysis, 2015 - ACS Publications
An in situ-generated complex from [RuCp* Cl2] 2 and dpePhos ligand is reported as an
efficient catalyst in the presence of 5 mol% of LiOtBu for the N-methylation of amines using …

Mechanistic evidence of a Ni (0/II/III) cycle for nickel photoredox amide arylation

RD Bradley, BD McManus, JG Yam… - Angewandte Chemie …, 2023 - Wiley Online Library
This work demonstrates the dominance of a Ni (0/II/III) cycle for Ni‐photoredox amide
arylation, which contrasts with other Ni‐photoredox C‐heteroatom couplings that operate via …

Copper-catalyzed C (aryl)–N bond formation

F Monnier, M Taillefer - Amination and Formation of sp2 CN Bonds, 2013 - Springer
Although requiring the use of stoichiometric amounts of metal and harsh conditions, the
copper-mediated coupling reactions of aryl halides with amines and phenols (Ullmann …

Metal-Free N-Arylation of Secondary Amides at Room Temperature

F Tinnis, E Stridfeldt, H Lundberg, H Adolfsson… - Organic …, 2015 - ACS Publications
The arylation of secondary acyclic amides has been achieved with diaryliodonium salts
under mild and metal-free conditions. The methodology has a wide scope, allows synthesis …

B2(OH)4-Mediated Reductive Transamidation of N-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis

J Bai, S Li, R Zhu, Y Li, W Li - The Journal of Organic Chemistry, 2023 - ACS Publications
We herein developed a reductive transamidation reaction between N-acyl benzotriazoles
(AcBt) and organic nitro compounds or NaNO2 under mild conditions. This protocol …

[PDF][PDF] Goldberg reaction: Development, mechanistic insights and applications

A Maria Thomas, A Sujatha… - Mini-Reviews in Organic …, 2015 - academia.edu
Cu-catalyzed N-arylation of amides commonly known as Goldberg reaction is an important
transformation in organic synthesis for the construction of pharmaceuticals and fine …

Visible light-induced amide bond formation

W Song, K Dong, M Li - Organic letters, 2019 - ACS Publications
A metal-, base-, and additive-free amide bond formation reaction was developed under an
organic photoredox catalyst. This green approach showed excellent functional selectivity …

Assembly of N,N-Disubstituted Hydrazines and 1-Aryl-1H-indazoles via Copper-Catalyzed Coupling Reactions

X Xiong, Y Jiang, D Ma - Organic letters, 2012 - ACS Publications
CuI-catalyzed coupling of N-acyl-N′-substituted hydrazines with aryl iodides takes place at
60–90° C to afford N-acyl-N′, N′-disubstituted hydrazines regioselectively and thereby …