title: Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles.
abstract: Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Marcus E
authors.initials: ME
authors.lastname: Farmer
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Xing
authors.initials: X
authors.lastname: Huo
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Pankaj
authors.initials: P
authors.lastname: Jain
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Peng-Xiang
authors.initials: PX
authors.lastname: Shen
authors.affiliation: Department of Medical Oncology, Dana-Farber Cancer Institute , 360 Longwood Avenue, Boston, Massachusetts 02115, United States.
authors.forename: Mette
authors.initials: M
authors.lastname: Ishoey
authors.affiliation: Department of Medical Oncology, Dana-Farber Cancer Institute , 360 Longwood Avenue, Boston, Massachusetts 02115, United States.
authors.forename: James E
authors.initials: JE
authors.lastname: Bradner
authors.affiliation: Chemical Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Steven R
authors.initials: SR
authors.lastname: Wisniewski
authors.affiliation: Chemical Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Martin D
authors.initials: MD
authors.lastname: Eastgate
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D008024:Ligands; D010636:Phenols / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D006571:Heterocyclic Compounds; D008024:Ligands; D010636:Phenols; D002244:Carbon; D006859:Hydrogen