title: Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.
abstract: Bismuth(III) acetate is a safe, inexpensive, and selective facilitator of sequential protodeboronations, which when used in conjunction with Ir-catalyzed borylations allows access to a diversity of borylated indoles. The versatility of combining Ir-catalyzed borylations with Bi(III)-catalyzed protodeboronation is demonstrated by selectively converting 6-fluoroindole into products with Bpin groups at the 4-, 5-, 7-, 2,7-, 4,7-, 3,5-, and 2,4,7-positions and the late-stage functionalization of sumatriptan.
authors.affiliation: Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
authors.forename: Fangyi
authors.initials: F
authors.lastname: Shen
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories , Rahway, New Jersey 07065, United States.
authors.forename: Sriram
authors.initials: S
authors.lastname: Tyagarajan
authors.affiliation: Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
authors.forename: Damith
authors.initials: D
authors.lastname: Perera
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories , Rahway, New Jersey 07065, United States.
authors.forename: Shane W
authors.initials: SW
authors.lastname: Krska
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories , Rahway, New Jersey 07065, United States.
authors.forename: Peter E
authors.initials: PE
authors.lastname: Maligres
authors.affiliation: Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
authors.forename: Milton R
authors.initials: MR
authors.lastname: Smith
authors.affiliation: Department of Chemistry, Michigan State University , 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
authors.forename: Robert E
authors.initials: RE
authors.lastname: Maleczka
mesh_terms: D000085:Acetates / Q000737:chemistry*; D001729:Bismuth / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000085:Acetates; D001896:Boron Compounds; D007211:Indoles; D001729:Bismuth