Compounds which contain the 1-heteroaryl-3-azabicyclo[3.1.0]hexane architecture are of particular interest to the pharmaceutical industry, yet remain a challenge to synthesize. We wish to disclose an expedient and modular approach to the synthesis of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes by Suzuki–Miyaura and Chan–Evans–Lam coupling reactions of tertiary trifluoroborate salts. Our Suzuki–Miyaura cross-coupling protocol is compatible with a broad range of aryl and heteroaryl bromides and chlorides. The unprecedented Chan–Evans–Lam coupling of tertiary trifluoroborates allows for the facile construction of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes containing C-tertiary arylamines at the ring juncture.

Construction of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes by sp2-sp3 Suzuki–Miyaura and Chan–Evans–Lam coupling reactions of tertiary trifluoroborates

254th National Meeting (2017)

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