title: Ligand-Enabled β-C-H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups.
abstract: Herein we report acid-directed β-C(sp3)-H arylation of α-amino acids enabled by pyridine-type ligands. This reaction does not require the installation of an exogenous directing group, is scalable, and enables the preparation of Fmoc-protected unnatural amino acids in three steps. The pyridine-type ligands are crucial for the development of this new C(sp3)-H arylation.
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Gang
authors.initials: G
authors.lastname: Chen
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Zhe
authors.initials: Z
authors.lastname: Zhuang
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Gen-Cheng
authors.initials: GC
authors.lastname: Li
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Tyler G
authors.initials: TG
authors.lastname: Saint-Denis
authors.affiliation: Chemical and Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, NJ, 08903, USA.
authors.forename: Yi
authors.initials: Y
authors.lastname: Hsiao
authors.affiliation: Chemical and Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, NJ, 08903, USA.
authors.forename: Candice L
authors.initials: CL
authors.lastname: Joe
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Jin-Quan
authors.identifier: 0000-0003-3560-5774
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D005449:Fluorenes; D006841:Hydrocarbons, Aromatic; D008024:Ligands; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D011725:Pyridines; D010165:Palladium; C023666:pyridine
keywords: C−H activation; amino acids; arylation; palladium; pyridine ligands