title: Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.
abstract: A direct oxidative C-H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C-H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated with good to high yields for numerous electron-rich and electron-poor substrates. Further reaction of selected products via Suzuki arylation and deacetylation provides access to highly functionalized indole structures.
authors.affiliation: Small Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Kyle
authors.initials: K
authors.lastname: Clagg
authors.affiliation: Small Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Haiyun
authors.initials: H
authors.lastname: Hou
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Adam B
authors.initials: AB
authors.lastname: Weinstein
authors.affiliation: Small Molecule Analytical Chemistry and Quality Control, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: David
authors.initials: D
authors.lastname: Russell
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
authors.affiliation: Small Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
authors.forename: Stefan G
authors.initials: SG
authors.lastname: Koenig
mesh_terms: D000586:Amination; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D007211:Indoles; D009942:Organometallic Compounds; C503382:indole-2-carboxylate; D010165:Palladium