title: One-pot C-N/C-C cross-coupling of methyliminodiacetic acid boronyl arenes enabled by protective enolization.
abstract: Iterative cross-coupling is a highly efficient and versatile strategy for modular construction in organic synthesis, though this has historically been demonstrated solely in the context of C-C bond formation. A C-N cross-coupling of haloarene methyliminodiacetic acid (MIDA) boronates with a wide range of aromatic and aliphatic amines is reported. Successful cross-coupling of aliphatic amines was realized only through protective enolization of the MIDA group. This reaction paradigm was subsequently utilized to achieve a one-pot C-N/C-C cross-coupling sequence.
authors.affiliation: Novartis Institutes for BioMedical Research, Inc., 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
authors.forename: Jonathan E
authors.initials: JE
authors.lastname: Grob
authors.forename: Michael A
authors.initials: MA
authors.lastname: Dechantsreiter
authors.forename: Ritesh B
authors.initials: RB
authors.lastname: Tichkule
authors.forename: Michael K
authors.initials: MK
authors.lastname: Connolly
authors.forename: Ayako
authors.initials: A
authors.lastname: Honda
authors.forename: Ronald C
authors.initials: RC
authors.lastname: Tomlinson
authors.forename: Lawrence G
authors.initials: LG
authors.lastname: Hamann
mesh_terms: D000588:Amines / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D007098:Imino Acids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000588:Amines; D001897:Boronic Acids; D007098:Imino Acids; C533766:N-methyliminodiacetic acid