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Updated: Jan 15, 2026

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Published on: July 30, 2017
Palladium-Catalyzed Benzylation/Semipinacol Rearrangement for the Construction of 3-Quaternary Carbon 2-Spiroindoline
Xin Chang1, Kun-Shan Xue1, Hai-Yan Tao1
1Hubei Research Center of Fundamental Science-Chemistry, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
None:
The 3-quaternary carbon 2-spiroindoline scaffold occupies a significant position in both medicinal and synthetic chemistry. While the dearomatization of indoles represents the most direct and efficient route to such structural units, considerable limitations persist. Herein, utilizing 2-cyclobutanol-3-substituted indoles and benzyl phosphates as model substrates, we developed a novel Pd/BEt3 synergistic catalyzed tandem benzylation/semipinacol rearrangement. This strategy efficiently constructs a series of 3-quaternary carbon 2-spiroindolines in high yields with excellent chemoselectivity and diastereoselectivity. Furthermore, this catalytic cascade reaction proceeds efficiently in a one-pot manner, as the thermally driven semipinacol rearrangement circumvents the need for intermediate isolation.
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