Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 35, Pages 4965-4969Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800341
Keywords
Earth-abundant metals; Alkynes; Isoquinolines; Annulation; Nickel; Regioselectivity
Categories
Funding
- National Natural Science Foundation of China [21702230]
- Natural Science Foundation of Jiangsu Province [BK20160743]
- Program for Jiangsu Province Innovative Research Team
- 111 Project [B16046]
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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 Et3N 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.
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