Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering, College of Chemistry, Peking University , Beijing, 100871, China.
Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.
A CuI-catalyzed A(3) (amines, aldehydes and alkynes) reaction of tetrahydroisoquinolines (THIQs), aldehydes, and alkynes to give C1-alkynylated THIQ products (endo-yne-THIQs) was developed. This redox neutral C1-alkynylation of THIQs, which was conducted under mild conditions, has a broad scope for the used aldehydes and alkynes. It was proposed that the A(3) reaction first generates in situ exo-iminium ions, which then isomerize to endo-iminium ions and react with copper acetylides to give the endo alkynylated THIQs (endo-yne-THIQs).
开发了一种铜催化的 A(3)（胺、醛和炔烃）反应，用于四氢异喹啉（THIQs）、醛和炔烃的反应，得到 C1-炔基化 THIQ 产物（内炔-THIQs）。这种温和条件下的 THIQs 的氧化还原中性 C1-炔基化反应，对所用醛和炔烃具有广泛的适用性。该反应首先生成原位的外亚胺离子，然后异构化为内亚胺离子，并与铜炔化物反应，得到内炔基化的 THIQs（内炔-THIQs）。
