Preparation of Polyfunctional Organozinc Halides by an InX<sub>3</sub>- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides

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6

作者:

AD BenischkeGreacuteG LexCorreProf.xP Knochel

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摘要:

A catalytic system consisting of InCl<sub>3</sub> (3&#x2005;mol&thinsp;%) and LiCl (30&#x2005;mol&thinsp;%) allows a convenient preparation of polyfunctional arylzinc halides via the insertion of zinc powder to various aryl iodides in THF at 50&thinsp;&deg;C in up to 95&thinsp;% 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&#x2005;mol&thinsp;%) and LiCl (150&#x2005;mol&thinsp;%), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50&thinsp;&deg;C, 2-18&#x2005;h). Alkyl bromides are also converted to the corresponding zinc reagents in the presence of In(acac)<sub>3</sub> (10&#x2005;mol&thinsp;%) and LiCl (150&#x2005;mol&thinsp;%) in 70-80&thinsp;% yield.

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DOI:

10.1002/chem.201605139

年份:

2017

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