通过使用多氟亚磺酰基作为辅助基团的钯催化 C-H 烯丙基化反应合成 N-无氢 1,4-二氢异喹啉-3(2)-酮。
Synthesis of N-H-Free 1,4-Dihydroisoquinoline-3(2)-ones via Pd-Catalyzed C-H Olefination Using Polyfluorosulfinyl as the Auxiliary Group.
机构信息
School of Biotech. & Health Sciences, Wuyi University, 22 Dongcheng Vill., Jiangmen, Guangdong 529020, China.
CAS Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, University of Chinese Academy of Sciences, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, China.
出版信息
Org Lett. 2020 Aug 7;22(15):5880-5884. doi: 10.1021/acs.orglett.0c01979. Epub 2020 Jul 29.
A Pd(II)-catalyzed olefination of aryl C-H bonds with a self-cleaving 2-chlorotretafluoroethylsulfinyl (-SOCFCFCl) auxiliary was developed. In the reaction mixture, the olefination products underwent Michael addition and the subsequent expulsion of the auxiliary to provide the N-H-free 1,4-dihydroisoquinoline-3(2)-one products. Mechanistic studies reveal that the auxiliary group is crucial for C-H activation, and NaCO and an alcoholic solvent play key roles in facilitating the cleavage of the polyfluoroalkylsulfinyl auxiliary.
Pd(II)催化的芳基 C-H 键与自裂解的 2-氯三氟乙基亚磺酰基（-SOCFCFCl）助剂的烯烃化反应得到发展。在反应混合物中，烯烃化产物经历迈克尔加成，随后辅助基团的消除提供了无 N-H 的 1,4-二氢异喹啉-3(2)-酮产物。机理研究表明，辅助基团对于 C-H 活化至关重要，而 NaCO 和醇溶剂在促进多氟烷基亚磺酰基的裂解中起着关键作用。
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