Rh(III)-Catalyzed One-Pot Three-Component Diannulation of Benzils, Ammonium Acetate, and Alkynes to Build 1,1?-Biisoquinolines

作者：Lv, Shihai; Tian, Ya-Nan; Yang, Yanyan; Wen, Chaoying; Li, Shiqing^*

来源：Journal of Organic Chemistry, 2022, 87(23): 16019-16025.

DOI：10.1021/acs.joc.2c02157

• C-H ACTIVATION
• HETEROCYCLE-FUSED PYRIDINES
• EXCITED-STATE PROPERTIES
• BOND ACTIVATION
• ISOQUINOLINES
• ARYL
• FUNCTIONALIZATION
• ORGANOCATALYSTS
• ANNULATION
• KETIMINES

An efficient one-pot synthesis of 1,1 '-biisoquinolines by a three-component reaction of commercially available raw materials (benzils, NH4OAc, and alkynes) is disclosed. This complicated reaction involves in situ diimine formation via benzil-NH4OAc condensation, Rh(III)-catalyzed 2-fold imine-directed C-H activation, and annulation with alkynes. Both symmetric and unsymmetric 1,1 '-biisoquino-lines could be assembled in moderate to high yields. The reaction mechanism is supported through ESI-MS, in which Cp*ClRh+, Cp*(OAc)Rh+, Cp*(OPiv)Rh+, and two rhodacycle intermediates are successfully detected to explain the evolution of rhodium species.

• 单位
  桂林理工大学