ABSTRACT
Phytic acid is abundant in various plant-based foods and is considered agricultural waste. Here, we demonstrate the effectiveness of this organophosphorus acid as a sustainable catalyst for the direct amination reactions of allylic alcohols. This approach is successfully performed in air using technical grade solvents, affording allylanilines in moderate to excellent yields. Challenging electron-rich anilines react effectively, and their corresponding Friedel-Crafts side products can be minimised under the optimised reaction conditions. A variety of asymmetrically substituted allylic alcohols are tolerated, while the scope is extended to amide, and C-, O- and S-nucleophiles.
ABSTRACT
Commercially available (aqueous) hypophosphorus acid is an efficient catalyst for the synthesis of α,ß-unsaturated carbonyl compounds from their corresponding propargylic alcohols. Reactions were carried out in technical toluene in the presence of air and in several instances the desired products were isolated analytically pure after a simple work-up.
ABSTRACT
A straightforward synthesis of aryl aziridines is reported from readily available azides and alkenes and using technical solvents in the presence of air. This methodology does not require any additives and the obtained compounds can be employed in ring-opening and ring-expansion reactions.
Subject(s)
Aziridines , Alkenes , Azides , Cycloaddition Reaction , Molecular Structure , StereoisomerismABSTRACT
The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions with N-nucleophiles of varying basicity is presented. A careful choice of the reaction conditions minimized undesired rearrangements and arylation processes, typical side reactions with Brønsted acid catalysis. These systems are compatible with technical solvents and presence of air, and they are also applicable to C-, O-, and S-nucleophiles.
