Lien vers Pubmed [PMID] – 34397167
Lien DOI – 10.1002/open.202100147
ChemistryOpen 2021 12; 10(12): 1166-1169
The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.