title: Harnessing C-H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization.
abstract: Ir-catalyzed deborylation can be used to selectively deuterate aromatic and heteroaromatic substrates. Combined with the selectivities of Ir-catalyzed C-H borylations, uniquely labeled compounds can be prepared. In addition, diborylation/deborylation reactions provide monoborylated regioisomers that complement those prepared by C-H borylation. Comparisons between Ir-catalyzed deborylations and Pd-catalyzed deborylations of diborylated indoles described by Movassaghi are made. The Ir-catalyzed process is more effective for deborylating aromatics and is generally more effective in the monodeborylation of diborylated thiophenes. These processes can be applied to complex molecules such as clopidogrel.
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Venkata A
authors.initials: VA
authors.lastname: Kallepalli
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Kristin A
authors.initials: KA
authors.lastname: Gore
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Feng
authors.initials: F
authors.lastname: Shi
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Luis
authors.initials: L
authors.lastname: Sanchez
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Ghayoor A
authors.initials: GA
authors.lastname: Chotana
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Susanne L
authors.initials: SL
authors.lastname: Miller
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Robert E
authors.initials: RE
authors.lastname: Maleczka
authors.affiliation: Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824-1322, United States.
authors.forename: Milton R
authors.initials: MR
authors.lastname: Smith
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry*; D004952:Esters; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001896:Boron Compounds; D001897:Boronic Acids; D004952:Esters; D007211:Indoles; D003903:Deuterium