Hong, Xi; Zhou, Quan; Huang, Shuang; Cui, He-Zhen; Li, Zhi-Ming; Hou, Xiu-Feng published the artcile< Transition metal catalyzed C7 and ortho-selective halogenation of 2-arylbenzo[d]oxazoles>, Application In Synthesis of 128-09-6, the main research area is halosuccinimide phenyl benzoxazole rhodium catalyst regioselective halogenation; halophenyl benzoxazole preparation; phenyl halo benzoxazole preparation.
A transition metal catalyzed chlorination, bromination and iodination of 2-arylbenzo[d]oxazole with N-halosuccinimide, in which ruthenium-catalyzed halogenation occurred on the C7-position and rhodium-catalyzed halogenation occurred on the ortho-position. The C7 halogenation was only observed for 5-methyl-2-(p-substituted)arylbenzo[d]oxazoles under rhodium catalysis. Preliminary mechanistic experiments and d. functional theory (DFT) calculations suggested that the C7-halogenation catalyzed by Ru might have a single-electron-transfer (SET) radical process, while the ortho-selective halogenation catalyzed by Rh proceeds probably through a redox-neutral SN2-type mechanism. The different selectivity of Rh catalyzed halogenation was due to the charge difference between benzo[d]oxazolyl and aryl rings. The two kinds of halogenated products were proved to be versatile by constructing aryl and alkynyl groups on the C-X site via Suzuki and Sonogashira cross-coupling reactions.
Organic Chemistry Frontiers published new progress about Benzoxazoles Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 128-09-6 belongs to class chlorides-buliding-blocks, and the molecular formula is C4H4ClNO2, Application In Synthesis of 128-09-6.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics