title: Sequential S(N)Ar Reaction/Suzuki-Miyaura Coupling/C-H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles.
abstract: A rapid synthesis of 1,3,4,5-tetraaryl-substituted pyrazoles has been achieved through a sequence of SN Ar reaction/Suzuki-Miyaura coupling/Pd-catalyzed direct arylations that used 3-iodo-1H-pyrazole as a scaffold. Pyrazoles with four different aryl groups were synthesized in a straightforward manner with no extra synthetic steps, such as protection/deprotection or the introduction of activating/directing groups, using readily available substrates and reagents. The developed synthetic approach enabled the structurally diverse synthesis of multiaryl-substituted pyrazoles without using a glovebox technique.
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8552, Japan.
authors.forename: Taiki
authors.initials: T
authors.lastname: Morita
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8552, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Kobayashi
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8552, Japan.
authors.forename: Keisuke
authors.initials: K
authors.lastname: Matsumura
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Johmoto
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8551, Japan.
authors.forename: Hidehiro
authors.initials: H
authors.lastname: Uekusa
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro-ku, Tokyo, 152-8552, Japan. sfuse@res.titech.ac.jp.|Chemical Resources Laboratory, Tokyo Institute of Technology, 4259, Nagatsuta-cho, Midori-ku, Yokohama, 226-8503, Japan. sfuse@res.titech.ac.jp.
authors.forename: Shinichiro
authors.initials: S
authors.lastname: Fuse
authors.affiliation: Yokohama College of Pharmacy, 601, Matano-cho, Totsuka-ku, Yokohama, Kanagawa, 245-0066, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006841:Hydrocarbons, Aromatic; D011720:Pyrazoles; D010165:Palladium
keywords: C-H activation; cross-coupling; heterocycles; palladium; synthetic methods