Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process

Ahmed Aliyenne (1) , Frédéric Pin (1) , Vijaykumar Nimbarte (1) , Ata Martin Lawson (1) , Sébastien Comesse (1) , Morgane Sanselme (2) , Vincent Tognetti (3) , Laurent Joubert (3) , Adam Daïch (1)

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire
2 SMS - Sciences et Méthodes Séparatives
3 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Isoindolinones and tricyclic N,O‐acetals are obtained from bis‐N‐acyliminium precursors and assorted nucleophiles using catalytic Bi(OTf)3. The reactions proceed, respectively, through a double amidoalkylation or tandem π‐cyclisation/α‐oxa‐amidoalkylation. Mechanistic aspects of the tandem chemistry are supported by DFT calculations and its utility in RCM and Click reactions illustrated. New 1,3‐bis‐N‐acyliminium species generated easily with nontoxic Bi(OTf)3 catalyst at very low loadings (2 mol‐%) were trapped inter‐ and intramolecularly with various poly‐nucleophiles. This mild, efficient, practical and general tandem approach provides an array of substituted isoindolinones and cyclic N,O‐acetals.

Domains: Chemical Sciences; Chemical Sciences; Cristallography; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Organic chemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Theoretical and/or physical chemistry

Ahmed Aliyenne, Frédéric Pin, Vijaykumar Nimbarte, Ata Martin Lawson, Sébastien Comesse, et al.. Bi(OTf) 3 -Catalysed Access to 2,3-Substituted Isoindolinones and Tricyclic N,O-Acetals by Trapping of Bis- N -Acyliminium Species in a Tandem Process. European Journal of Organic Chemistry, 2016, 2016 (21), pp.3592-3602. ⟨10.1002/ejoc.201600530⟩. ⟨hal-01928678⟩