Visible-Light-Mediated Intermolecular [2 + 2]-Cycloaddition Reaction of 3-Alkylideneindolin-2-one with Alkenes via Triplet Energy Transfer for the Synthesis of 3-Spirocyclobutyl Oxindoles

Shao-Xian Shi; Huan-Huan Zhang; Yi-Lin Wang; Lin-Hong Jiang; Peng-Fei Xu; Yong-Chun Luo

doi:10.1021/acs.orglett.3c01695

Visible-Light-Mediated Intermolecular [2 + 2]-Cycloaddition Reaction of 3-Alkylideneindolin-2-one with Alkenes via Triplet Energy Transfer for the Synthesis of 3-Spirocyclobutyl Oxindoles

Org Lett. 2023 Jul 28;25(29):5426-5430. doi: 10.1021/acs.orglett.3c01695. Epub 2023 Jul 17.

Authors

Shao-Xian Shi¹, Huan-Huan Zhang¹, Yi-Lin Wang¹, Lin-Hong Jiang¹, Peng-Fei Xu^{1

2}, Yong-Chun Luo^{1

2}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
² State Key Laboratory of Veterinary Etiological Biology, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou 730000, P. R. China.

PMID: 37458365
DOI: 10.1021/acs.orglett.3c01695

Abstract

[2 + 2]-Cycloaddition is the most straightforward approach to the construction of cyclobutanes. In this paper, the intermolecular [2 + 2]-cycloaddition reaction of 3-alkylideneindolin-2-ones with alkenes was achieved. This reaction can be used in the synthesis of 3-spirocyclobutyl oxindoles, polycyclic oxindoles, and late stage modification of some drug molecules.