Preparation of Polyfunctional Organozinc Halides by an InX3- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides

Benischke, Andreas D.; Le Corre, Gregoire and Knochel, Paul (2017): Preparation of Polyfunctional Organozinc Halides by an InX3- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides. In: Chemistry-A European Journal, Vol. 23, No. 4: pp. 778-782

Abstract

A catalytic system consisting of InCl3 (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 degrees 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)(3) (3 mol%) and LiCl (150 mol%), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50 degrees C, 2-18 h). Alkyl bromides are also converted to the corresponding zinc reagents in the presence of In(acac)(3) (10 mol%) and LiCl (150 mol%) in 70-80% yield.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0947-6539
• Language: English