Journal of Molecular Catalysis A: Chemical Pub Date : 2016-07-07 , DOI: 10.1016/j.molcata.2016.07.013 Birgit Gröll , Patricia Schaaf , Marko D. Mihovilovic , Michael Schnürch
A facile and efficient method to introduce alkyne groups to the C-1 position of biologically interesting 1,2,3,4-tetrahydroisoquinolines via direct CH-functionalization is reported. Various alkynylated N-substituted 1,2,3,4-tetrahydroisoquinolines could be obtained by using copper(I)-chloride as catalyst, alkynoic acids as alkyne source and t-BuOOH as oxidant, in a one-pot two-step decarboxylation- alkynylation reaction in moderate to high yields. Furthermore, a one-pot protocol of a three-step decarboxylation-alkynylation-1,3-dipolar cycloaddition reaction leading to 1-triazolyl-tetrahydroisoquinolines was developed, a hitherto unknown reaction cascade.
中文翻译:
Cu(I)在1,2,3,4-四氢异喹啉上催化一锅脱羧-炔基反应和一锅合成三唑基1,2,3,4-四氢异喹啉
据报道,通过直接的C H-官能化将炔基引入生物学上有趣的1,2,3,4-四氢异喹啉的C-1位置的简便有效的方法。通过一锅两步脱羧反应,以氯化铜(I)为催化剂,炔酸为炔烃源,t-BuOOH为氧化剂,可以制得各种炔基化的N-取代的1,2,3,4-四氢异喹啉。中度到高产率的炔基化反应。此外,开发了导致1-三唑基-四氢异喹啉的三步脱羧-炔基-1,3-偶极环加成反应的一锅法方案,这是迄今未知的反应级联。