A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process

Xin-Xing Wu; Hui Tian; Yu Wang; Anjia Liu; Hengfan Chen; Zhixiang Fan; Xuefeng Li; Shufeng Chen

doi:10.1039/C8QO00964C

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A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process†

Xin-Xing Wu,

*^a Hui Tian,‡^a Yu Wang,‡^a Anjia Liu,‡^a Hengfan Chen,^a Zhixiang Fan,^a Xuefeng Li^a and Shufeng Chen

*^a

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* Corresponding authors

^a Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, P. R. China
E-mail: wuxinxng@163.com, shufengchen@imu.edu.cn

Abstract

A novel construction of azaindoline functionalized spirocarbocyclic scaffolds bearing two all-carbon quaternary centers has been developed via a palladium-catalyzed Heck cyclization/phenol dearomatization reaction. In the cascade process, three new C(sp²)–C(sp³) bonds are formed in a single chemical operation. The approach shows broad substrate scope and good functional-group tolerance.

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DOI: https://doi.org/10.1039/C8QO00964C
Article type: Research Article
Submitted: 05 Sep 2018
Accepted: 07 Oct 2018
First published: 09 Oct 2018

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Org. Chem. Front., 2018,5, 3310-3314

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A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process

X. Wu, H. Tian, Y. Wang, A. Liu, H. Chen, Z. Fan, X. Li and S. Chen, Org. Chem. Front., 2018, 5, 3310 DOI: 10.1039/C8QO00964C

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Organic Chemistry Frontiers

A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process†

Abstract

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A facile approach to synthesize azaindoline functionalized spirocarbocyclic scaffolds via a Pd-catalyzed cascade cyclization/dearomatization process

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