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. 2022 Oct 10;12(44):28800-28803.
doi: 10.1039/d2ra05387j. eCollection 2022 Oct 4.

PIFA-mediated selenylative spirocyclization of indolyl ynones: facile access to selenated spiro[cyclopentenone-1,3'-indoles]

Zhichao Chen  1 , Jingjing Li  1 , Wenting Weng  1 , Xiaolan Xie  1 , Jian Lei  1
Affiliations

PIFA-mediated selenylative spirocyclization of indolyl ynones: facile access to selenated spiro[cyclopentenone-1,3'-indoles]

Zhichao Chen et al. RSC Adv. .

Abstract

A fast selenylative spirocyclization of indolyl ynones mediated by PIFA has been developed. This transformation was enabled by the reactive RSeOCOCF3 species generated in situ from diselenides with PIFA, involving an electrophilic dearomative cascade cyclization. This protocol provides a facile and efficient method for the synthesis of selenated spiro[cyclopentenone-1,3'-indoles] and tolerates broad functional groups.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of selenated spiroindolenines via radical or ionic process.
Scheme 2
Scheme 2. Control experiments.
Scheme 3
Scheme 3. Proposed reaction mechanism.
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