[Zurück]

B. Gröll, P. Schaaf, M.D. Mihovilovic, M. Schnürch:
"Cu(I)-catalyzed one-pot decarboxylation-alkynylation reactions on1,2,3,4-tetrahydroisoquinolines and one-pot synthesis oftriazolyl-1,2,3,4-tetrahydroisoquinolines";
Journal of Molecular Catalysis A: Chemical, 426 (2017), S. 398 - 406.

A facile and efficient method to introduce alkyne groups to the C-1 position of biologicallyinteresting 1,2,3,4-tetrahydroisoquinolines via direct CH-functionalization is reported. Various alkyny-lated N-substituted 1,2,3,4-tetrahydroisoquinolines could be obtained by using copper(I)-chlorideas catalyst, alkynoic acids as alkyne source and t-BuOOH as oxidant, in a one-pot two-stepdecarboxylation- alkynylation reaction in moderate to high yields. Furthermore, a one-pot protocolof a three-step decarboxylation-alkynylation-1,3-dipolar cycloaddition reaction leading to 1-triazolyl-tetrahydroisoquinolines was developed, a hitherto unknown reaction cascade.

Click reaction / Copper catalysis / Cross dehydrogenative coupling / One-pot reaction / Domino catalysis

http://dx.doi.org/10.1016/j.molcata.2016.07.013