Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides

This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)-NHC catalysts demonstrate superior reactivity in chemoselective Suzuki-Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.

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Publication Details

Journal
Organic Letters
Published
2025-09-04
DOI
https://doi.org/10.1021/acs.orglett.5c03118
Citations
1
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
0.94

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article

Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides

Nana Chen, Jin Zhang, Ruihong Wang, Michal Szostak et al.
1 citations
Organic Letters
Catalytic Cross-Coupling Reactions
0.94
article

Structurally Flexible (Thiazol-2-ylidene)Pd(Allyl)Cl Complexes for Suzuki–Miyaura Cross-Coupling of Aryl Halides and Amides

Nana Chen, Jin Zhang, Ruihong Wang, Michal Szostak, Xiao Han, Li Sun, Gaopeng Zhang
article en
1 citations

Abstract

This study introduces a new class of (NHC)Pd(allyl)Cl complexes featuring thiazol-2-ylidene ligands, which exhibit enhanced steric and electronic properties compared to those of traditional imidazol-2-ylidenes. These air-stable Pd(II)-NHC catalysts demonstrate superior reactivity in chemoselective Suzuki-Miyaura cross-couplings of aryl bromides and amides. Kinetic studies reveal their superior reactivity over traditional imidazol-2-ylidene-based complexes. The findings highlight the potential of thiazole-based carbenes in advancing Pd-catalyzed cross-coupling reactions.

Organic LettersVol. 27(36)
Rutgers, The State University of New Jersey (US), Rutgers Sexual and Reproductive Health and Rights (NL), Catalytic Materials (United States) (US), Kaili University (CN), Shaanxi University of Science and Technology (CN)
Rutgers, The State University of New Jersey, National Natural Science Foundation of China, China Postdoctoral Science Foundation, Education Department of Shaanxi Province, National Institute of General Medical Sciences
Openalex Percentile: Top 22%
Catalytic Cross-Coupling Reactions
0.94
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