title: Cine substitution of arenes using the aryl carbamate as a removable directing group.
abstract: An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionalization. The removal of aryl carbamates is achieved by employing an air-stable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Tehetena
authors.initials: T
authors.lastname: Mesganaw
authors.forename: Noah F
authors.initials: NF
authors.lastname: Fine Nathel
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
chemical_list: D002219:Carbamates; D007211:Indoles; D009532:Nickel