Mannich reactions of resin-bound substrates: 2. A versatile three-component solid-phase organic synthesis methodology

Visual detection of formaldehyde by highly selective fluorophore labeling via gold(iii) complex-mediated three-component coupling reaction

“…To facilitate the washing step, the sterically bulky amines were attached to polymer-bound 2-chlorotrityl chloride resins to give resinlinked sterically bulky amine 1e according to literature. 9 The A 3 -coupling reaction of formaldehyde, resin-linked sterically bulky amine 1e, and coumarin-linked alkyne 2c gave fluorescent propargylamines (Scheme 4). The A 3 -coupling reactions of formaldehyde (0.02 mmol), resin-linked sterically bulky amine 1e (15 mg), coumarin-linked alkyne 2c (0.02 mmol) and bis-cyclometallated gold(III) catalyst 3a (0.01 mmol) were conducted in 1,2-dichloroethane at 50 °C for 1 h to give resin-bound propargylamine 4c (Scheme 4).…”

Recent Advances in the A3 Coupling Reactions and their Applications

“…Synthesis of propargylamine through three component coupling of a terminal alkyne, secondary amine and formaldehyde was first reported in 1953 by Guermont . In 1998, Dax et al reported a solid‐phase three component coupling of aldehydes, secondary amines and alkynes in the presence of excess CuCl (2 equiv.). In 2002, Li et al first introduced the term “A 3 coupling” for the synthesis of propargylamine derivatives using various Cu‐ and Ru‐catalysts .…”

Progress in Synthesis of Propargylamine and Its Derivatives by Nanoparticle Catalysis via A3 coupling: A Decade Update

“…Three component synthesis of propargylamine was first shown long back by Guermont and co‐workers in 1953 by using terminal alkyne, secondary amine and formaldehyde . Later on, Dax et al had reported solid phase synthesis of propargylamine in the year 1998 . However, the term “A3 coupling” was first introduced by Li et al in 2002 when they had done lots of work with Copper catalyst along with Ruthenium .…”