Remote C(sp3)–H activation: palladium-catalyzed intermolecular arylation and alkynylation with organolithiums and terminal alkynes

Peng Chen; Zhi-Yong Wang; Jia-Xin Wang; Xiao-Shui Peng; Henry N. C. Wong

doi:10.1039/D2QO00584K

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Remote C(sp³)–H activation: palladium-catalyzed intermolecular arylation and alkynylation with organolithiums and terminal alkynes†

Peng Chen,^a Zhi-Yong Wang,^a Jia-Xin Wang,^b Xiao-Shui Peng

*^ab and Henry N. C. Wong

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China
E-mail: xspeng@cuhk.edu.cn, hncwong@cuhk.edu.hk, hncwong@cuhk.edu.cn

^b School of Science and Engineering, The Chinese University of Hong Kong (Shenzhen), Longgang District, Shenzhen, China

Abstract

A 1,4-palladium shift is regarded as one of the solutions towards the challenging remote C(sp³)–H activation. Herein, we report two efficient remote C(sp³)–H activation protocols involving palladium-catalyzed C(sp³)–C(sp²) and C(sp³)–C(sp) cross-coupling with aryllithium reagents and terminal alkynes as key coupling partners, respectively. More than 50 examples with acceptable to high yields, good functional group tolerance, and high regioselectivities are presented. The practicality of the reaction is demonstrated in a gram-scale manner.

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DOI: https://doi.org/10.1039/D2QO00584K
Article type: Research Article
Submitted: 13 Apr 2022
Accepted: 30 Apr 2022
First published: 03 May 2022

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Org. Chem. Front., 2022,9, 3438-3445

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Remote C(sp³)–H activation: palladium-catalyzed intermolecular arylation and alkynylation with organolithiums and terminal alkynes

P. Chen, Z. Wang, J. Wang, X. Peng and H. N. C. Wong, Org. Chem. Front., 2022, 9, 3438 DOI: 10.1039/D2QO00584K

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