Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation.

Chem Soc Rev

Zientzia eta Teknologia Fakultatea, Euskal Herriko Unibertsitatea, P.O. Box 644, 48080, Bilbao, Spain.

Published: April 2008

Palladium and copper-catalysed arylation of amines, alcohols and thiols, powerful tools for the construction of C-N, C-O and C-S bonds, are typically carried out in organic (and often toxic) solvents. Therefore the use of such a sustainable, benign solvent as water in this context has gained growing attention. This tutorial review presents the most recent advances dealing with palladium and copper-catalysed carbon-heteroatom bond formation performed in total or partial aqueous media. The particular and distinctive features of water which are apparently responsible for the acceleration and greater chemoselectivity of the aqueous protocols will also be discussed.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b709565cDOI Listing

Publication Analysis

Top Keywords

palladium copper-catalysed
12
copper-catalysed arylation
8
carbon-heteroatom bond
8
bond formation
8
arylation reactions
4
reactions presence
4
presence water
4
water focus
4
focus carbon-heteroatom
4
formation palladium
4

Similar Publications

Article Synopsis
  • The copper-catalysed azide-alkyne cycloaddition (CuAAC) and sulfur-fluoride exchange (SuFEx) processes have limitations, such as difficulty in modifying triazole rings or selectively functionalizing SuFEx connectors.
  • A new strategy, bisphosphine-copper-catalysed phenoxydiazaborinine formation (CuPDF), integrates multiple compounds into a versatile link that can be modified in situ.
  • CuPDF and another method, copper- and palladium-catalysed quinoline formation (Cu/PdQNF), are easy to perform, applicable in aqueous environments, and enable the creation of tunable fluorescent hubs and complex oligomers without protection groups.
View Article and Find Full Text PDF

Transition metal-catalysed C-H functionalization reactions are one of the most efficient synthetic methodologies to construct carbon-carbon and carbon-heteroatom bonds. The initial developments in the field were largely dominated by expensive transition metal catalysts. However, in the past decade, the focus of the catalyst shifted to first-row transition metals and copper catalysis contributed significantly.

View Article and Find Full Text PDF

Chemistry on the Complex: Derivatization of TiO N -Based Complexes and Application to Multi-Step Synthesis.

Chemistry

December 2021

Laboratoire de Synthèse et fonctions des Architectures Moléculaires, Université de Strasbourg, CNRS, CMC UMR 7140, 67000, Strasbourg, France.

The chemistry on octahedral TiO N -complexes is described. The Ti(IV)-based precursors are composed of two 3,3'-diphenyl-2,2'-biphenolato ligands (1) and one substituted 1,10-phenanthroline ligand (2-5). The application of imine condensation, palladium-catalyzed C-C bond formation or copper-catalysed azide-alkyne cycloaddition allowed the grafting of various new groups onto these species.

View Article and Find Full Text PDF

Advances in palladium-catalysed imidoylative cyclization of functionalized isocyanides for the construction of N-heterocycles.

Org Biomol Chem

August 2021

State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China and University of Chinese Academy of Sciences, Beijing 100049, China and Bioland Laboratory (Guangzhou Regenerative Medicine and Health Guangdong Laboratory), Guangzhou 510005, China.

Palladium-catalysed isocyanide insertion reactions have witnessed great progress in recent years. In particular, imidoylative cyclization of functionalized isocyanides was successfully developed by taking advantage of the adjustable substituents on the isocyano group, opening a new avenue to access a variety of nitrogen-containing heterocycles. In this review article, we summarize the advances of functionalized isocyanide insertion reactions and highlight the breakthroughs of enantioselective palladium catalysed imidoylation reactions by using this strategy.

View Article and Find Full Text PDF

The total synthesis of K-252c (staurosporinone) a sequential C-H functionalisation strategy.

Chem Sci

April 2016

Department of Chemistry , Department of Cambridge , Lensfield Road , Cambridge , CB2 1EW , UK . Email:

A synthesis of the bioactive indolocarbazole alkaloid K-252c (staurosporinone) a sequential C-H functionalisation strategy is reported. The route exploits direct functionalisation reactions around a simple arene core and comprises of two highly-selective copper-catalysed C-H arylations, a copper-catalysed C-H amination and a palladium-catalysed C-H carbonylation, which build up the structural complexity of the natural product framework.

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!