title: Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.
abstract: A Pd-catalyzed/N-heterocycle-directed C(sp(3) )-H olefination has been developed. The monoprotected amino acid ligand (MPAA) is found to significantly promote Pd-catalyzed C(sp(3) )-H olefination for the first time. Cu(OAc)2 instead of Ag(+) salts are used as the terminal oxidant. This reaction provides a useful method for the synthesis of alkylated pyrazoles.
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Weibo
authors.initials: W
authors.lastname: Yang
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
authors.forename: Shengqing
authors.initials: S
authors.lastname: Ye
authors.affiliation: Medicinal Chemistry, Vertex Pharmaceuticals, 11010 Torreyana Rd., San Diego, CA, 92121, USA.
authors.forename: Yvonne
authors.initials: Y
authors.lastname: Schmidt
authors.affiliation: Medicinal Chemistry, Vertex Pharmaceuticals, 11010 Torreyana Rd., San Diego, CA, 92121, USA.
authors.forename: Dean
authors.initials: D
authors.lastname: Stamos
authors.affiliation: Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA. yu200@scripps.edu.
authors.forename: Jin-Quan
authors.initials: JQ
authors.lastname: Yu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D008024:Ligands; D016877:Oxidants / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000475:Alkenes; D008024:Ligands; D016877:Oxidants; D011720:Pyrazoles; D010165:Palladium
keywords: C−H activation; amino acid ligands; olefination; organic chemistry; pyrazole