Halogen bond-catalyzed Pictet–Spengler reaction
Mattis Damrath, Alessandra Döring, Boris J. Nachtsheim
Abstract
-protected tryptamines and diverse carbonyl compounds (aromatic, heteroaromatic, and aliphatic aldehydes) into the corresponding tetrahydro-β-carbolines (THβCs) in up to 98% yield. The reaction versatility was further demonstrated by a successful oxa-variant using tryptophol. Control experiments revealed the crucial role of halogen bonding in ensuring efficient reaction progress.
Topics & Concepts
CatalysisHalogenChemistryCombinatorial chemistryPictet–Spengler reactionOrganic chemistryAlkylSynthesis and Biological ActivityChemical Synthesis and ReactionsOxidative Organic Chemistry Reactions