Efficient ruthenium and copper cocatalzyed five-component coupling to form dipropargyl amines under mild conditions in water

Abstract

Dipropargyl amines are synthesized by a double direct alkynylation of primary followed by secondary imines formed in situ during an efficient, five-component, one-pot coupling reaction cocatalyzed by ruthenium and copper in water.

Copper‐Catalyzed Four‐Component Coupling between Aldehydes, Amines, Alkynes, and Carbon Dioxide

“…[8] As a natural extension of the A 3 -coupling reaction, we have begun to explore the possibility of incorporating the A 3 -coupling methodology into tandem processes. With respect to this goal, we have recently reported a five-component double A 3 -coupling [9] and a six-component double A 3 -coupling/A C H T U N G -T R E N N U N G [2+2+2] cycloaddition reaction. [10] While a great deal of progress has been achieved in the A 3 -coupling reaction, there exist some limitations to the current methodology.…”

Unorthodox chemistry for an unorthodox challenge: Exploration of new chemical reactivities for a sustainable future

“…one pot under mild conditions in water under an atmosphere of air [127]. Tetrasubstituted isoindolines can be synthesized readily from three alkyne units, two aqueous formaldehyde units and a primary amine in a single synthetic operation via a six-component coupling by using a combined copper/rhodium catalyst (eq.…”

Synthetic Chemistry with an Eye on Future Sustainability

“…However, with this system, the terminal alkyne is limited to trimethylsilyacetylene [91b]. Using our ruthenium-copper co-catalyst system, a five-component double aldehyde-alkyne-amine coupling was developed to synthesize various dipropargylamines from a range of simple amines, aldehydes, and alkynes in one pot under mild conditions in water under an atmosphere of air (Scheme 19.41) [112]. The reaction yield was better than in toluene at room temperature.…”