The consideration of discrete variables (e.g. catalyst, ligand, solvent) in experimental self-optimization approaches remains a significant challenge. Herein we report the application new mixed variable multi-objective optimization (MVMOO) algorithm for chemical reactions. Coupling MVMOO with an automated continuous flow platform enabled identification trade-off curves different performance cri...

With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. One process of particular interest is the direct nucleophilic substitution of an alcohol avoiding its preliminary tr...

Isocyanides are important building blocks in organic synthesis; however, their synthesis is time and resource consuming often unpleasant due to smelly nature. Diversification of isocyanides can be accomplished by de novo or from already existing isocyanides. In this work, we report for the first-time isocyanide diversification based on nucleophilic aromatic substitution suitable precursor The m...

This review article is dedicated to special polysaccharide esters – the toluenesulfonic acid (tosylates) and carbonate esters. After describing specifics of synthesis, particular emphasis placed on use tosylates phenyl carbonates for subsequent modification by nucleophilic substitution (SN) reactions. For this purpose, advantages limitations respective derivatives are discussed with regard thei...

2-Halogeno BODIPYs undergo copper catalysed nucleophilic substitution with alkyl amines and anilines and an amide to give the corresponding 3-aminoBODIPY derivatives. The substrates are readily prepared by the regioselective 2-halogenation of the chemically robust, preformed BODIPYs thus providing an alternative to direct nucleophilic substitution of the corresponding 3-halogenoBODIPYs which re...

4-Nitro-1,8-naphthalic anhydride (NNA) was used to distinguish cysteine from homocysteine and other potentially interfering thiols through a novel sequential substitution mechanism. The discrimination involves a blue-fluorescent thioether formation via nucleophilic aromatic substitution of the nitro group by thiol, followed by a second intramolecular nucleophilic aromatic substitution of alkylt...

Figure 1: Directed aromatic functionalization methods. The title of this Thematic Series brings to the minds of most organic chemists the beautifully logical aromatic electrophilic substitution (SEAr) [1-5] and, to a lesser extent, nucleophilic aromatic substitution (SNAr) [2,6,7] reactions as taught to many generations of students in their first organic chemistry courses [8] (Figure 1). Being ...