β-Selective C-H arylation of thiophenes enabled by α-diimine palladium catalysts
In this study, a series of sterically and electronically tunable acenaphthene-based α-diimine palladium complexes were synthesized and characterized. These complexes were evaluated as catalysts for the β-C-H arylation of thiophene derivatives with arylboronic acids under aerobic conditions. Among th...
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| Published in | Tetrahedron Vol. 186; p. 134872 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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01.11.2025
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| Abstract | In this study, a series of sterically and electronically tunable acenaphthene-based α-diimine palladium complexes were synthesized and characterized. These complexes were evaluated as catalysts for the β-C-H arylation of thiophene derivatives with arylboronic acids under aerobic conditions. Among them, complex C3, featuring a 3,5-dimethyl-substituted N-aryl moiety, exhibited the highest catalytic activity. Under optimized conditions, C3 enabled the β-selective arylation of a broad scope of thiophene substrates bearing electron-donating and electron-withdrawing substituents, affording the desired products in good to excellent yields. The reaction proceeded efficiently with low catalyst loading and demonstrated high functional group tolerance. This study presents a practical and general catalytic strategy for site-selective C–H functionalization of heteroarenes under mild, air-stable conditions.
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•Tunable α-diimine ligands control the steric and electronic properties of Pd catalysts.•Efficient C-H arylation achieved with 2 mol% catalyst under base-free conditions.•Broad scope with thiophenes and arylboronic acids; exclusive β-selectivity observed.•Bench-stable Pd precatalysts and simple setup enable practical and scalable reactions. |
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| AbstractList | In this study, a series of sterically and electronically tunable acenaphthene-based α-diimine palladium complexes were synthesized and characterized. These complexes were evaluated as catalysts for the β-C-H arylation of thiophene derivatives with arylboronic acids under aerobic conditions. Among them, complex C3, featuring a 3,5-dimethyl-substituted N-aryl moiety, exhibited the highest catalytic activity. Under optimized conditions, C3 enabled the β-selective arylation of a broad scope of thiophene substrates bearing electron-donating and electron-withdrawing substituents, affording the desired products in good to excellent yields. The reaction proceeded efficiently with low catalyst loading and demonstrated high functional group tolerance. This study presents a practical and general catalytic strategy for site-selective C–H functionalization of heteroarenes under mild, air-stable conditions.
[Display omitted]
•Tunable α-diimine ligands control the steric and electronic properties of Pd catalysts.•Efficient C-H arylation achieved with 2 mol% catalyst under base-free conditions.•Broad scope with thiophenes and arylboronic acids; exclusive β-selectivity observed.•Bench-stable Pd precatalysts and simple setup enable practical and scalable reactions. |
| ArticleNumber | 134872 |
| Author | Wang, Ke Liu, Feng-Shou Zeng, Qing-Zhao |
| Author_xml | – sequence: 1 givenname: Qing-Zhao surname: Zeng fullname: Zeng, Qing-Zhao – sequence: 2 givenname: Ke surname: Wang fullname: Wang, Ke – sequence: 3 givenname: Feng-Shou surname: Liu fullname: Liu, Feng-Shou email: fengshou2004@126.com |
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| Title | β-Selective C-H arylation of thiophenes enabled by α-diimine palladium catalysts |
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