Palladium-Catalyzed Oxidative Cross-Coupling of Arylhydrazines and Arenethiols with Molecular Oxygen as the Sole Oxidant.

J Org Chem

Key Laboratory of Chemical Biology of Jiangxi Province, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P. R. China.

Published: February 2018

A highly efficient palladium-catalyzed oxidative cross-coupling of arylhydrazines and arenethiols with molecular oxygen as the sole oxidant to afford unsymmetrical diaryl sulfides has been developed. The only byproducts are nitrogen and water. A broad range of functional groups, even the reactive iodides, are tolerated and thus offer the opportunity for further functionalization.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.7b02926DOI Listing

Publication Analysis

Top Keywords

palladium-catalyzed oxidative
8
oxidative cross-coupling
8
cross-coupling arylhydrazines
8
arylhydrazines arenethiols
8
arenethiols molecular
8
molecular oxygen
8
oxygen sole
8
sole oxidant
8
oxidant highly
4
highly efficient
4

Similar Publications

We report the synthesis of N-capped peptides under mild conditions using the oxidative aminocarbonylation of aryl iodides and peptide esters as nucleophiles in the solution phase. Ex situ chloroform in chamber A generates CO, which diffuses to chamber B, which contains other reactants. This method offers N-capped peptides at 80 °C for 12 h.

View Article and Find Full Text PDF

Palladium-Catalyzed Oxidative Allene-Allene Cross-Coupling.

J Am Chem Soc

January 2025

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-10691 Stockholm, Sweden.

Direct cross-coupling reactions between two similar unactivated partners are challenging but constitute a powerful strategy for the creation of new carbon-carbon bonds in organic synthesis. [4]Dendralenes are a class of acyclic branched conjugated oligoenes with great synthetic potential for the rapid generation of structural complexity, yet the chemistry of [4]dendralenes remains an unexplored field due to their limited accessibility. Herein, we report a highly selective palladium-catalyzed oxidative cross-coupling of two allenes with the presence of a directing olefin in one of the allenes, enabling the facile synthesis of a broad range of functionalized [4]dendralenes in a convergent modular manner.

View Article and Find Full Text PDF

An aryl radical assay is used to provide information about the formation of aryl radicals from aryl halides in coupling reactions to arenes in the presence of palladium sources and under LED irradiation (λ = 456 nm). The assay uses 2-halo--xylenes as substrates. Aryl radical formation is indicated both by a defined product composition and by signature deuterium isotope effects.

View Article and Find Full Text PDF

Under most conditions, 2,4-dihalopyrimidines undergo substitution reactions at C4. Here we report that Pd(II) precatalysts supported by bulky -heterocyclic carbene ligands uniquely effect C2-selective cross-coupling of 2,4-dichloropyrimidine with thiols. The regioselectivity of this reaction stands in stark contrast to ∼1500 previously reported Pd-catalyzed cross-couplings that favor C4 in the absence of other substituents on the pyrimidine ring.

View Article and Find Full Text PDF

Theoretical Studies on the Reaction Mechanism for the Cycloaddition of Zwitterionic π-Allenyl Palladium Species: Substrate-Controlled Isomerization.

Molecules

December 2024

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Zwitterionic π-allenyl palladium species are newly developed intermediates. A substrate-controlled step existed in the cycloaddition of zwitterionic π-allenyl palladium species with tropsulfimides or tropones. With the assistance of previously experimental studies, zwitterionic allenyl/propargyl palladium species was provenly found by HRMS.

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!