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© Research
Publication : ChemistryOpen

Direct Synthesis of Allyl Amines with 2‐Nitrosulfonamide Derivatives via the Tsuji‐Trost Reaction

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in ChemistryOpen - 15 Aug 2021

Link to Pubmed [PMID] – 29178406

Link to DOI – 10.1002/open.202100147

Bon, C. et al. L. Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction. ChemistryOpen n/a (n/a). https://doi.org/10.1002/open.202100147.

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. A direct method for the allylation of 2‐nitrosulfonamides is described and exemplified. The mild and flexible conditions used as well as the ease to remove the 2‐nitrosulfonamide group are compatible with a large set of chemical moieties.

https://www.researchgate.net/publication/353926570_Direct_Synthesis_of_Allyl_Amines_with_2-Nitrosulfonamide_Derivatives_via_the_Tsuji-Trost_Reaction