Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles via C–H/N–H bond functionalizations

Zhangpei Chen; Zhiqiang Ding; Tian Chen; Lingxin Meng; Gongshu Wang

doi:10.1039/D0OB01899F

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Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles via C–H/N–H bond functionalizations†

Zhangpei Chen,

*^a Zhiqiang Ding,^a Tian Chen,^a Lingxin Meng^a and Gongshu Wang^a

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* Corresponding authors

^a Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, P. R. China
E-mail: chenzhangpei@mail.neu.edu.cn

Abstract

An efficient method for the construction of various pyrazolo[5,1-a]isoquinolines has been achieved via Ru(II)-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles. This oxidant-free transformation occurred through pyrazole-directed C–H activation, Ru-carbene insertion, and acid-promoted carbonyl condensation processes, enabling dual C–C and C–N bond formation. A broad substrate scope with respect to both coupling components worked efficiently with high yields.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB01899F
Article type: Paper
Submitted: 15 Sep 2020
Accepted: 09 Oct 2020
First published: 09 Oct 2020

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Org. Biomol. Chem., 2020,18, 8486-8490

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Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles via C–H/N–H bond functionalizations

Z. Chen, Z. Ding, T. Chen, L. Meng and G. Wang, Org. Biomol. Chem., 2020, 18, 8486 DOI: 10.1039/D0OB01899F

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Organic & Biomolecular Chemistry

Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles via C–H/N–H bond functionalizations†

Abstract

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Ruthenium-catalyzed α-carbonyl sulfoxonium ylide annulations with aryl substituted pyrazoles via C–H/N–H bond functionalizations

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