Versatile halogenation via a CNHC^Csp3 palladacycle intermediate

Qiaoqiao Teng; Ziwei Liu; Haobin Song; Jiayu Liu; Yaru Zhao; Weihua Jiang; Han Vinh Huynh; Qi Meng

doi:10.1039/D3DT00113J

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Versatile halogenation via a C_NHC^C_sp3 palladacycle intermediate†

Qiaoqiao Teng,

*^a Ziwei Liu,^a Haobin Song,^a Jiayu Liu,^a Yaru Zhao,^a Weihua Jiang,^a Han Vinh Huynh

*^b and Qi Meng*^a

Author affiliations

* Corresponding authors

^a Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, China
E-mail: tqq@cczu.edu.cn, mengqi@cczu.edu.cn

^b Department of Chemistry, National University of Singapore, 117543 Singapore, Republic of Singapore
E-mail: chmhhv@nus.edu.sg

Abstract

Stable cyclopalladated complexes containing an (sp³)C–Pd bond were synthesized via α-CH₂ deprotonation and palladation of N-alkyl groups of carbene ligands bearing electron-withdrawing substituents. The strong electron donating strengths of the resulting C_NHC^C_sp3 chelators were experimentally identified, and the palladacycle underwent template-directed, versatile C-halogenation with X₂.

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Article information

DOI: https://doi.org/10.1039/D3DT00113J
Article type: Communication
Submitted: 13 Jan 2023
Accepted: 06 Feb 2023
First published: 07 Feb 2023

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Dalton Trans., 2023,52, 2223-2226

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Versatile halogenation via a C_NHC^C_sp3 palladacycle intermediate

Q. Teng, Z. Liu, H. Song, J. Liu, Y. Zhao, W. Jiang, H. V. Huynh and Q. Meng, Dalton Trans., 2023, 52, 2223 DOI: 10.1039/D3DT00113J

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