Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 7, Pages 3065-3072Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400057t
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Funding
- National Basic Research Program of China [2010CB833300]
- National Natural Science Foundation of China [21172218]
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An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.
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