College of Chemistry and Chemical Engineering, Qingdao University, Qingdao 266071, China.
Org Lett. 2022 Aug 26;24(33):6148-6153. doi: 10.1021/acs.orglett.2c02303. Epub 2022 Aug 11.
Despite the great advancement in atroposelective synthesis in the past decades, the enantioselective synthesis of 2,2'-difluoro-1-biaryls is unprecedented. Herein, a palladium and chiral amino acid catalyzed atroposelective C-H olefination to construct the axially chiral 2,2'-difluoro-1-biaryls is reported. A variety of polyfluoro-substituted biaryls were forged under mild conditions in good yields with excellent enantioselectivity (up to 99% ee). The potential application was demonstrated by a gram-scale synthesis and synthetic transformations.
尽管在过去几十年中，在手性选择性合成方面取得了巨大进展，但 2,2'-二氟-1-联苯的对映选择性合成仍是前所未有的。在此，我们报道了钯和手性氨基酸催化的轴手性 C-H 烯烃化反应，用于构建轴向手性 2,2'-二氟-1-联苯。在温和条件下，通过克级合成和合成转化，以优异的对映选择性（高达 99%ee）获得了多种多氟取代的联苯。
