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钯催化的立体选择性脱氟芳基化/烯基化/烷基化 - 二氟环丙烷。

Palladium-Catalyzed Stereoselective Defluorination Arylation/Alkenylation/Alkylation of -Difluorinated Cyclopropanes.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM , University of Science and Technology of China , Hefei 230026 , China.

出版信息

Org Lett. 2019 Jul 19;21(14):5645-5649. doi: 10.1021/acs.orglett.9b01979. Epub 2019 Jul 9.

DOI:10.1021/acs.orglett.9b01979
PMID:31287696
Abstract

A palladium-catalyzed cross-coupling of -difluorinated cyclopropanes with boronic acids, providing the corresponding arylated/alkenylated/alkylated 2-fluoroallylic scaffolds, is generated. This new approach has good functional group compatibility for both -difluorinated cyclopropanes and boronic acids; thus, an array of synthetic building blocks of monofluoroalkene scaffolds including conjugated fluorodiene and skipped fluorodiene gave good yields with high -selectivity. Moreover, proficient application was described for monofluoroalkene, whereas the corresponding alkyl fluoride was constructed through hydrogenation.

摘要

钯催化的 -二氟环丙烷与硼酸的交叉偶联反应,生成相应的芳基化/烯基化/烷基化 2-氟烯丙基骨架。这种新方法对 -二氟环丙烷和硼酸都具有良好的官能团兼容性;因此,一系列包括共轭氟二烯和缺氟二烯的单氟烯烃骨架的合成砌块都以高产率和高选择性得到。此外,还描述了该方法在单氟烯烃中的有效应用,而相应的烷基氟化物则通过氢化反应构建。

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