Cobalt-Catalyzed alpha-Arylation of Substituted alpha-Bromo alpha-Fluoro beta-Lactams with Diaryl Zinc Reagents: Generalization to Functionalized Bromo Derivatives

作者:Lorion, MM (Lorion, Melanie M.)[ 1 ] ; Koch, V (Koch, Vanessa)[ 1,2 ] ; Nieger, M (Nieger, Martin)[ 4 ] ; Chen, HY (Chen, Hi-Yung)[ 5 ] ; Lei, AW (Lei, Aiwen)[ 5 ] ; Brase, S (Braese, Stefan)[ 2,3 ] ; Cossy, J (Cossy, Janine)[ 1 ]

CHEMISTRY-A EUROPEAN JOURNAL

卷: 26 期: 58 页: 13163-13169

DOI: 10.1002/chem.202001721

出版年: OCT 15 2020

在线发表日期: SEP 2020

文献类型:Article

摘要

A cobalt-catalyzed cross-coupling of alpha-bromo alpha-fluoro beta-lactams with diarylzinc or diallylzinc reagents is herein disclosed. The protocol proved to be general, chemoselective and operationally simple allowing the C4 functionalization of beta-lactams. The substrate scope was expanded to alpha-bromo lactams and amides, alpha-bromo lactones and esters as well asN- and O-containing heterocycles.

关键词

作者关键词:beta-lactam; bis(organo)zinc reagents; catalysis; cobalt; cross-coupling

KeyWords Plus:CROSS-COUPLING REACTIONS; AMIDES

作者信息

通讯作者地址:

Centre National de la Recherche Scientifique (CNRS) PSL Univ, CNRS, ESPCI Paris, Mol Macromol Chem & Mat C3M, 10 Rue Vauquelin, F-75231 Paris 05, France.

通讯作者地址: Cossy, J (通讯作者)

PSL Univ, CNRS, ESPCI Paris, Mol Macromol Chem & Mat C3M, 10 Rue Vauquelin, F-75231 Paris 05, France.

地址:

[ 1 ]‎ PSL Univ, CNRS, ESPCI Paris, Mol Macromol Chem & Mat C3M, 10 Rue Vauquelin, F-75231 Paris 05, France

[ 2 ]‎ Karlsruhe Inst Technol KIT, Inst Organ Chem IOC, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany

[ 3 ]‎ Karlsruhe Inst Technol KIT, Inst Biol & Chem Syst IBCS FMS, Hermann von Helmholtz Pl 1, D-76344 Eggenstein Leopoldshafen, Germany

[ 4 ]‎ Univ Helsinki, Dept Chem, POB 55, Helsinki 00014, Finland

[ 5 ]‎ Wuhan Univ, Inst Adv Studies, Wuhan 430072, Peoples R China

电子邮件地址:janine.cossy@espci.fr