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Studies Pertaining to the Diastereoselective Fischer Indolization and Exploration of Aryl Carbamates in Nickel-Catalyzed Reactions

  • Author(s): Mesganaw, Tehetena
  • Advisor(s): Garg, Neil K
  • et al.

Chapter one provides a concise review of nickel- and iron-catalyzed cross-couplings of unconventional phenolic derivatives. The review summarizes carbon-carbon, carbon¬-nitrogen, and carbon-hydrogen bond forming reactions developed in our group. Chapter two describes our exploration of interrupted Fischer indolization methodology. This was examined in the formal syntheses of physovenine and debromoflustramine B, and in the synthesis of the communesin scaffold. Enantioselective and diastereoselective variants of the interrupted Fischer indolization reaction is also reported.

Chapters three, four, and five are a discussion of our work in the field of nickel-catalyzed cross-coupling reactions of phenol derivatives. The use of aryl carbamates and sulfamates in the Ni(0)- and Ni(II)-catalyzed amination is described in chapters three and four. A synthetic application to synthesize polysubstituted aromatics is also reported. A computational mechanistic study for the Ni(0)-catalyzed amination of aryl carbamates is included. Chapter five describes the reductive cleavage of aryl carbamates. When employed after ortho-functionalization of the aryl carbamate, a net cine substitution can be achieved.

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