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Three-component dicarbofunctionalization of allylamines <i>via</i> nucleopalladation pathway: unlocking vicinal and geminal selectivity

Nityananda Ballav, Shib Nath Saha, Shailesh Yadav, Mahiuddin Baidya

2024Chemical Science17 citationsDOIOpen Access PDF

Abstract

a Pd(ii)/Pd(0) reaction modality resulted in geminal selectivity. The protocol is operationally simple, scalable, and offers two distinct types of products bearing functionalized tryptamine and bisindolyl frameworks in very high to excellent yields. The reaction features a wide substrate generality and also remains effective in the presence of various medicinally relevant scaffolds. Notably, this work represents the first example of nucleopalladation-guided intermolecular dicarbofunctionalization of allylamines.

Topics & Concepts

GeminalVicinalSelectivityComponent (thermodynamics)ChemistryStereochemistryOrganic chemistryPhysicsQuantum mechanicsCatalysisCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling Reactions