3 years ago

Construction of 1-Heteroaryl-3-azabicyclo[3.1.0]hexanes by sp3–sp2 Suzuki–Miyaura and Chan–Evans–Lam Coupling Reactions of Tertiary Trifluoroborates

Construction of 1-Heteroaryl-3-azabicyclo[3.1.0]hexanes by sp3–sp2 Suzuki–Miyaura and Chan–Evans–Lam Coupling Reactions of Tertiary Trifluoroborates
Michael R. Harris, Qifang Li, Jun Xiao, Yajing Lian, Allyn T. Londregan
Compounds that 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 report herein 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 the facile construction of 1-heteroaryl-3-azabicyclo[3.1.0]hexanes containing C-tertiary arylamines at the ring juncture.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01097

DOI: 10.1021/acs.orglett.7b01097

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