I2-mediated oxidative dearomatization for the synthesis of spirooxindole-lactones in water

Zan Liu; Longxia Jia; Pan Zhou; Yingru Xu; Yunlu Du; Haojie Guo; Can Zhang; Meizhou Zhang; Bin Wang; Dangui Wang

doi:10.1039/D5CC07384G

I₂-mediated oxidative dearomatization for the synthesis of spirooxindole-lactones in water

Zan Liu,

†^a Longxia Jia,†^a Pan Zhou,

†^a Yingru Xu,^c Yunlu Du,^a Haojie Guo,^a Can Zhang,^a Meizhou Zhang,*^b Bin Wang*^ad and Dangui Wang

*^a

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* Corresponding authors

^a School of Pharmacy, Shandong Second Medical University, Weifang 261053, China
E-mail: binwang@sdsmu.edu.cn, wangdangui@sdsmu.edu.cn

^b School of Life Science and Technology, Wuhan Polytechnic University, Wuhan 430024, China
E-mail: meizhouzhang@whpu.edu.cn

^c School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China

^d Affiliated Hospital of Shandong Second Medical University, Shandong Second Medical University, Weifang 261053, China

Abstract

We present an I₂-mediated oxidative dearomatization of carboxylic acid-tethered indole derivatives, enabling the synthesis of diverse spirooxindole-lactones in water. Isotope labelling studies demonstrated a dual role for water, acting as both reaction medium and oxygen source of oxindole. The low E-factor and high EcoScale further highlight the synthetic utility of this system.

Chemical Communications

I₂-mediated oxidative dearomatization for the synthesis of spirooxindole-lactones in water

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I₂-mediated oxidative dearomatization for the synthesis of spirooxindole-lactones in water

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