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

Author:
Harris, Michael R., Li, Qifang, Lian, Yajing, Xiao, Jun, Londregan, Allyn T.
Source:
Organic letters 2017 v.19 no.9 pp. 2450-2453
ISSN:
1523-7052
Subject:
Suzuki reaction, chemical structure, chlorides, organobromine compounds, pharmaceutical industry
Abstract:
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.
Agid:
5794078