钯催化2-芳基氮嘧啶与重氮酯和环醚三组分偶联合成叔胺酰胺的区域和立体选择性。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-12 DOI:10.1021/acs.orglett.5c01268

Xiaonan Mu,Yulong Niu,Minhui Guan,Hao Chen,Lei Wang

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引用次数: 0

摘要

报道了钯催化的2-芳基肼、α-重氮酯和环醚的三组分偶联反应，得到了具有优异区域选择性和立体选择性的叔胺酰胺。这种区域选择性开环反应不同于传统的过渡金属/膦催化的开环反应。广泛的底物可耐受（多达33例）。1,1'-双-2-萘酚（BINOL）衍生的磷酰胺配体的萘环上的邻芳基取代基对这种偶联至关重要，而附加的二膦（DPEphos）配体可以进一步提高反应活性。机理研究表明，10元和9元palladacycle中间体可能形成，随后发生两次可逆的β-H消除。

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Pd-Catalyzed Regio- and Stereoselective Synthesis of Tertiary Enamides via a Three-Component Coupling of 2-Arylaziridines with Diazo Esters and Cyclic Ethers.

A palladium-catalyzed three-component coupling of 2-arylaziridines, α-diazo esters, and cyclic ethers, affording tertiary enamides with excellent regio- and stereoselectivity, is reported. This regioselective ring-opening of aziridines is different from the classical transition-metal/phosphine catalyzed ones. A broad spectrum of substrates is tolerated (up to 33 examples). An ortho-aryl substituent on the naphthyl ring of 1,1'-bi-2-naphthol (BINOL)-derived phosphoramidite ligand is critical for this coupling, and the additional diphosphine (DPEphos) ligand can further enhance the reactivity. Mechanistic studies suggest that 10-membered and 9-membered palladacycle intermediates may be formed and followed by twice reversible β-H eliminations.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.