State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, People's Republic of China.
Org Lett. 2017 Jan 6;19(1):110-113. doi: 10.1021/acs.orglett.6b03385. Epub 2016 Dec 14.
A new method for the synthesis of δ- and α-carbolines through Ni-catalyzed [2 + 2 + 2] cycloaddition of ynamide-nitriles or alkyne-cyanamides with alkynes has been developed. The catalytic system of NiCl(DME)/dppp/Zn with a low-cost Ni(II)-precursor was first utilized in Ni-catalyzed [2 + 2 + 2] cycloaddition reactions, and the in situ generated Lewis acid may play an important role for the successful transformation. Not only internal alkynes but also terminal alkynes undergo the desired cycloaddition reactions efficiently to furnish the carboline derivatives with wide diversity and functional group tolerance.
一种通过镍催化的[2+2+2]环加成反应，从炔酰胺-腈或炔基-氰酰胺与炔烃合成δ-和α-咔啉的新方法已经被开发出来。该催化体系首次使用了成本较低的 Ni(II)-前体 NiCl(DME)/dppp/Zn 来催化[2+2+2]环加成反应，原位生成的路易斯酸可能对成功转化起着重要作用。不仅内部炔烃，而且末端炔烃也能有效地进行所需的环加成反应，得到具有广泛多样性和官能团容忍度的咔啉衍生物。
