Evidence map›Paper›PMID 37298843›Full record

ArticleMolecules (Basel, Switzerland)2023

A General Synthesis of Cross-Conjugated Enynones through Pd Catalyzed Sonogashira Coupling with Triazine Esters.

Dezhi Lin, Yunfang Liu, Hongyu Yang, Xiao Zhang, Huaming Sun, Yajun Jian, Weiqiang Zhang, Jianming Yang, Ziwei Gao

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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5 · Who and what money

Authors and funding

9 authors.

Dezhi LinKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Yunfang LiuSouth China Institute of Environmental Science, Ministry of Ecology and Environment, Guangzhou 510655, China.

Hongyu YangKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Xiao ZhangKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.ORCID 0000-0002-4310-4649

Huaming SunKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Yajun JianKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Weiqiang ZhangKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.ORCID 0000-0001-8810-9606

Jianming YangXi'an Modern Chemistry Research Institute, Xi'an 710065, China.

Ziwei GaoKey Laboratory of Applied Surface and Colloid Chemistry (MOE), Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China.

Funding

Key Research and Development Project of Shaanxi Science and Technology Department 2017SF-064National Natural Science Foundation of China 22171173the 111 Project B14041

6 · The paper itself

Abstract

The palladium-catalyzed Sonogashira coupling of α, β-unsaturated acid derivatives offers a diversity-oriented synthetic strategy for cross-conjugated enynones. However, the susceptibility of the unsaturated C-C bonds adjacent to the carbonyl group toward Pd catalysts makes the direct conversion of α, β-unsaturated derivatives as acyl electrophiles to cross-conjugated ketones rare. This work presents a highly selective C-O activation approach to prepare cross-conjugated enynones using α, β-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free conditions, NHC-Pd(II)-Allyl precatalyst alone catalyzed the cross-coupling of α, β-unsaturated triazine esters with terminal alkynes efficiently, yielding 31 cross-conjugated enynones with diverse functional groups. This method demonstrates the potential of triazine-mediated C-O activation for preparing highly functionalized ketones.

Indexed as

EstersPalladiumAlkynesCatalysisKetonesAlkynesEstersKetonesPalladiumC-O activationcross-couplingketone synthesispalladium catalysis

Identifiers

PMID37298843

DOI10.3390/molecules28114364

PMCPMC10254696

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