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百万分之一级钯催化的链烯醇区域选择性远程芳基化反应。

Ppm level palladium catalyzed regioselective remote arylation of alkenyl alcohols.

作者信息

Liu Chong, Wang Ling, Ge Haibo

机构信息

Department of Chemistry and Biochemistry, Texas Tech University Lubbock Texas 79409 USA

Residual Department, Merieux Testing Technology (Qingdao) Co., Ltd Qingdao 266000 China.

出版信息

Chem Sci. 2025 Jun 3. doi: 10.1039/d5sc02745d.


DOI:10.1039/d5sc02745d
PMID:40496502
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12147037/
Abstract

Recent studies highlight the importance and application of parts per million (ppm) palladium concentration in catalytic reactions. Lowering catalyst loading minimizes costs, simplifies purification, and reduces metal contamination, making it highly attractive for pharmaceutical and fine chemical manufacturing. Here, we report a ppm level Pd-catalyzed remote arylation reaction of alkenols, achieving high efficiency, regioselectivity, and flexible carbonyl scaffold construction. Notably, this strategy exhibits excellent compatibility with styrene-derived substrates and has been successfully achieved on a gram scale, providing a solid foundation for potential large-scale applications.

摘要

近期研究突出了百万分之一(ppm)钯浓度在催化反应中的重要性及应用。降低催化剂负载量可将成本降至最低、简化纯化过程并减少金属污染,这使其对制药和精细化学品制造极具吸引力。在此,我们报道了一种ppm级钯催化的链烯醇远程芳基化反应,该反应实现了高效、区域选择性以及灵活的羰基骨架构建。值得注意的是,此策略与苯乙烯衍生的底物具有出色的兼容性,并且已成功实现克级规模反应,为潜在的大规模应用奠定了坚实基础。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/ef678d9981eb/d5sc02745d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/f5b7f10d68b7/d5sc02745d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/7e323e3d78a5/d5sc02745d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/58d1fad26302/d5sc02745d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/ef678d9981eb/d5sc02745d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/f5b7f10d68b7/d5sc02745d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/7e323e3d78a5/d5sc02745d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/58d1fad26302/d5sc02745d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50ae/12242973/ef678d9981eb/d5sc02745d-s4.jpg

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Ppm level palladium catalyzed regioselective remote arylation of alkenyl alcohols.

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本文引用的文献

[1]
Facile construction of distal and diversified tertiary and quaternary stereocenters.

Proc Natl Acad Sci U S A. 2024-12-17

[2]
Ni-catalysed remote C(sp)-H functionalization using chain-walking strategies.

Nat Rev Chem. 2024-11

[3]
Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.

Nat Commun. 2024-6-27

[4]
Regiodivergent C-H Functionalization via Ni-Catalyzed Chain-Walking Reactions.

JACS Au. 2023-11-28

[5]
NiH-Catalyzed Functionalization of Remote and Proximal Olefins: New Reactions and Innovative Strategies.

Acc Chem Res. 2022-12-6

[6]
Nickel-Catalyzed Enantioselective Reductive Conjugate Arylation and Heteroarylation via an Elementary Mechanism of 1,4-Addition.

J Am Chem Soc. 2022-11-9

[7]
Recent advances in cobalt-based catalysts for efficient electrochemical hydrogen evolution: a review.

Dalton Trans. 2022-10-18

[8]
Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Org Process Res Dev. 2022-8-19

[9]
Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.

Chem Sci. 2022-4-25

[10]
Pd-Catalyzed Site-selective β- and γ-C(sp)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

J Am Chem Soc. 2022-3-23

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