Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst

We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthia-zoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Bronsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.

Automated summary

A new method was developed in this study using bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation, leading to the cascade olefination reaction of nine different methyl N-heteroarenes and providing high yields and (E)-selectivities in synthesizing N-heteroaryl stilbenoids without the need for transition-metal salt, ligand, stoichiometric base, or oxidant under mild conditions.