通过使用自裂解多氟乙基亚磺酰基导向基团的 Pd(II)催化 C(sp)-H 烯烃化反应合成 γ-内酰胺。
Synthesis of γ-Lactams via Pd(II)-Catalyzed C(sp)-H Olefination Using a Self-Cleaving Polyfluoroethylsulfinyl Directing Group.
机构信息
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 Rd., Shanghai 200032, China.
School of Biotechnology & Health Sciences, Wuyi University, 22 Dongcheng Vill., Jiangmen, Guangdong 529020, China.
出版信息
Org Lett. 2020 Sep 18;22(18):7141-7146. doi: 10.1021/acs.orglett.0c00326. Epub 2020 Sep 2.
A monodentate directing group, 2-chlorotetrafluoroethylsulfinylmide (-NHSOCFCFCl), for inert C(sp)-H bond activation is reported. This directing group shows efficient ability in Pd(II)-catalyzed C(sp)-H olefination. The desired olefination products undergo subsequent Michael addition and expulsion of the auxiliary to provide the free NH γ-lactam products. Preliminary mechanistic studies reveal that the auxiliary group is crucial for C(sp)-H activation.
报道了一种用于惰性 C(sp)-H 键活化的单齿导向基团 2-氯四氟乙基亚磺酰亚胺（-NHSOCFCFCl）。该导向基团在 Pd(II)催化的 C(sp)-H 烯烃化反应中表现出高效的能力。所需的烯烃化产物随后进行迈克尔加成反应和辅助基团的消除，以提供游离的 NH γ-内酰胺产物。初步的机理研究表明，辅助基团对于 C(sp)-H 活化至关重要。
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