This process demonstrates efficient synthesis of BINAM derivatives from naphthylamines, highlighting the role of copper and π systems in the reaction.
In this study, we report the efficient synthesis of 1,1'-binaphthyl-2,2'-diamine (BINAM) derivatives via copper-catalyzed oxidative coupling of 2-aminonaphthalenes. The use of a ligand featuring an extended π system in combination with Cu(II) and molecular oxygen as the terminal oxidant enabled the formation of various BINAM derivatives in yields of up to 84%. Mechanistic investigations suggest a redox pathway involving Cu(II)/Cu(I) cycling, and π-π interactions between the ligand and substrate are proposed to stabilize reactive intermediates, thereby contributing to the observed efficiency.
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Lee et al. (2025) studied this question.
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