Intermolecular Selective 1,2-Aminohydroxylation of 1,3-Dienes Enabled by Palladium/Copper/Oxygen Cooperation.

Xuan Yang, Yanbo Wang, Yunyi Li, Ke Wen, Huikang Liu, Jiatong Zhang, Zhengxing Wu, Zehua Yang, Wanbin Zhang

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Article in Precision chemistry, 2026. 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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9 authors.

Xuan YangHunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Institute of Pharmacy & Pharmacology School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421001, China.

Yanbo WangShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Yunyi LiShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Ke WenShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Huikang LiuShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Jiatong ZhangShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Zhengxing WuShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.

Zehua YangHunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, Institute of Pharmacy & Pharmacology School of Pharmaceutical Science, Hengyang Medical School, University of South China, Hengyang, Hunan 421001, China.ORCID https://orcid.org/0000-0001-9672-8204

Wanbin ZhangShanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China.ORCID https://orcid.org/0000-0002-4788-4195

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

β-Amino alcohols are important structural motifs that are widely present in pharmaceutical molecules and natural products with significant biological activities, making the development of synthetic methodologies for their preparation a long-standing research focus. Among current synthetic approaches, 1,2-aminohydroxylation of alkenes offers a direct route to β-amino alcohols. In particular, metal-catalyzed 1,2-aminohydroxylation of alkenes represents an efficient methodology. However, existing methods are restricted to intramolecular reactions or rely on either directing groups or active reagents (preoxidized nitrogen sources or special oxidants). Therefore, the development of a more general catalytic system that does not require intramolecular reactions, directing groups, or active reagents has remained highly desirable. Herein, we report an intermolecular selective 1,2-aminohydroxylation of 2,3-disubstituted 1,3-dienes enabled by palladium/copper/oxygen cooperation, using a simple nitrogen source. Notably, for 2,3-dialkyl-1,3-dienes bearing different alkyl groups, this aminohydroxylation enables alkyl recognition, favoring the less-hindered double bond with moderate to good chemoselectivity. This methodology provides a direct and powerful route to the synthesis of β-amino alcohols.

Indexed as

1,3-dieneaminohydroxylationcopperoxygenpalladium

Identifiers

PMID42820055

DOI10.1021/prechem.6c00059

PMCPMC13625911

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