A simple procedure for polymer-supported N-heterocyclic carbene silver complex via click chemistry: an efficient and recyclable catalyst for the one-pot synthesis of propargylamines

Abstract

A series of polymer-supported N-heterocyclic carbene silver complexes were prepared using a simple procedure via click chemistry. These complexes were tested as catalysts in the synthesis of propargylamines by the one-pot three-component coupling reaction of aldehydes, amines and alkynes (A(3)-coupling). The reaction was preceded smoothly to afford the corresponding products in good to excellent yields at room temperature under low catalyst loading of 0.1 mol%. Furthermore, the catalysts were stable and recoverable for six runs without a significant loss in their activity.

N-heterocyclic carbene gold(i) and silver(i) complexes bearing functional groups for bio-conjugation

“…However, unlike previously reported ligands of this type, 40 the target alkyne functionalized heterocycles 5-7 demanded more aggressive conditions to complete the reaction. Refluxing an imidazole with 4-bromobut-1-yne in toluene for 3 d provides the corresponding imidazolium salt (Eq.…”

Recent Advances in the A3 Coupling Reactions and their Applications

“…Despite plethora of new homogeneous and heterogeneous catalysts have been prepared and applied in the A 3 coupling reactions for the construction of propargylamines, but no metal coordinating polymers were reported till recently. In 2012, Cai and co‐workers introduced a polymer‐supported N ‐heterocyclic carbene (NHC) silver complex 31 as an efficient and recyclable catalyst for the synthesis of propargylamines (Scheme ). The NHC‐silver complex catalyst was prepared via a “click chemistry” approach.…”

Silver and gold-catalyzed multicomponent reactions

“…Moreover, the PS–NHC–Ag(I) catalyst was proven to be reusable at least 12 times without a significant loss of its catalytic activity. Similar PS–NHC–silver complexes were recently prepared via click-chemistry, and their aptitude to catalyze A 3 -coupling was verified [13]. …”