Preparation of Polyfunctional Organozinc Halides by an InX<sub>3</sub>- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides
摘要:
A catalytic system consisting of InCl<sub>3</sub> (3 mol %) and LiCl (30 mol %) allows a convenient preparation of polyfunctional arylzinc halides via the insertion of zinc powder to various aryl iodides in THF at 50 °C in up to 95 % yield. The use of a THF/DMPU (1:1) mixture shortens the reaction rates and allows the preparation of keto-substituted arylzinc reagents. In the presence of In(acac)<sub>3</sub> (3 mol %) and LiCl (150 mol %), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50 °C, 2-18 h). Alkyl bromides are also converted to the corresponding zinc reagents in the presence of In(acac)<sub>3</sub> (10 mol %) and LiCl (150 mol %) in 70-80 % yield.
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DOI:
10.1002/chem.201605139
年份:
2017
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