Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines.
1-Boryl- and 1,3-diborylisoindoles were synthesized by the palladium-catalyzed reaction of isoindolines with pinacolborane via sequential dehydrogenation and C-H borylation. Selective formation of the borylated isoindoles was achieved using Pd(dba)(2)/Me(2)S as the catalyst, in which Me(2)S suppressed the formation of 1-boryl-4,5,6,7-tetrahydroisoindoles. Diborylisoindole was cross-coupled with iodobenzene, giving 1,3-diphenylisoindole in high yield.
Ohmura
Toshimichi
T
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. ohmura@sbchem.kyoto-u.ac.jp
Kijima
Akihito
A
Suginome
Michinori
M
D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D007211:Indoles / Q000737:chemistry*; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D001896:Boron Compounds; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D010165:Palladium