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Highly Regioselective Isoquinoline Synthesis via Nickel‐Catalyzed Iminoannulation of Alkynes at Room Temperature
Author(s) -
Sun JianGuo,
Zhang XiaoYu,
Yang Hua,
Li Ping,
Zhang Bo
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800341
Subject(s) - isoquinoline , chemistry , regioselectivity , catalysis , nickel , annulation , combinatorial chemistry , organic chemistry
A simple and cost‐efficient nickel catalytic system for the annulation of 2‐haloaldimines with alkynes to synthesize 3,4‐disubstituted and 3‐substituted isoquinolines at room temperature has been developed. The air‐stable and inexpensive Ni(dppe)Cl 2 was employed as a precatalyst, and Et 3 N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one‐pot three‐component direct synthesis of isoquinolines starting with simple 2‐halobenzaldehydes, tert ‐butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.