Recyclable Palladium-Catalyzed Carbonylative Cyclization of Trifluoroacetimidoyl Chlorides with Nitro Compounds Towards 2-(Trifluoromethyl)quinazolin-4(3H)-ones

IF 2.3 4区化学 Q3 CHEMISTRY, PHYSICAL

Catalysis Letters Pub Date : 2025-10-04 DOI:10.1007/s10562-025-05180-9

Jinbiao Wu, Jianan Zhan, Mingzhong Cai

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引用次数: 0

Abstract

A new mesoporous SBA-15-anchored Schiff base and phosphine mixed bidentate palladium(II) complex [SBA-15-N, P-PdCl₂] was prepared via immobilization of 3- aminopropyltriethoxysilane on SBA-15, followed by condensation with 2–(diphenylphosphino)benzaldehyde and then coordination with PdCl₂. With the use of 5 mol% of SBA15-N, P-PdCl₂ as catalyst, the carbonylative cyclization between trifluoroacetimidoyl chlorides and nitro compounds proceeds smoothly in 1,4-dioxane at 120 °C with Na₂CO₃ (2 equiv.) as base by using Mo(CO)₆ (2 equiv.) as both a solid CO source and a reductant, yielding a variety of 2-(trifluoromethyl)quinazolin-4(3H)-ones in 68–94% yields. The SBA-15-N, P-PdCl₂ complex can be easily separated by a simple centrifugation process and recycled more than 8 cycles without a remarkable loss of activity. The current protocol not only solves the basic problem of expensive palladium catalyst recovery and reuse, but also prevents palladium contamination in the final product.

Graphical Abstract

A highly efficient heterogeneous palladium-catalyzed carbonylative cyclization of trifluoroacetimidoyl chlorides, nitro compounds and Mo(CO)6 towards 2-(trifluoro- methyl)quinazolin-4(3H)-ones is described.

Abstract Image

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可回收钯催化的三氟乙酰胺酰氯与硝基化合物羰基环化制2-（三氟甲基）喹唑啉-4(3H)-酮

采用3-氨基丙基三乙氧基硅烷固定SBA-15，与2 -（二苯基膦）苯甲醛缩合，再与PdCl2配位，制备了一种新型介孔SBA-15锚定的希夫碱-膦混合双齿钯配合物[SBA-15- n， P-PdCl2]。以5 mol%的SBA15-N， P-PdCl2为催化剂，以Na2CO3（2等量）为碱，Mo(CO)6（2等量）作为固体CO源和还原剂，在120℃的1,4-二氧六烷中顺利进行了三氟乙酰氯与硝基化合物之间的羰基环化反应，产率为68-94%。SBA-15-N， P-PdCl2配合物可以通过简单的离心分离过程很容易地分离出来，并且可以循环使用8次以上而没有明显的活性损失。目前的方案既解决了昂贵的钯催化剂回收和再利用的基本问题，又防止了最终产品中的钯污染。摘要描述了钯催化的三氟乙酸酰氯、硝基化合物和Mo(CO)6对2-（三氟-甲基）喹唑啉-4(3H)- 1的高效非均相羰基环化反应。

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来源期刊

Catalysis Letters 化学-物理化学

CiteScore

5.70

自引率

3.60%

发文量

327

审稿时长

1 months

期刊介绍： Catalysis Letters aim is the rapid publication of outstanding and high-impact original research articles in catalysis. The scope of the journal covers a broad range of topics in all fields of both applied and theoretical catalysis, including heterogeneous, homogeneous and biocatalysis. The high-quality original research articles published in Catalysis Letters are subject to rigorous peer review. Accepted papers are published online first and subsequently in print issues. All contributions must include a graphical abstract. Manuscripts should be written in English and the responsibility lies with the authors to ensure that they are grammatically and linguistically correct. Authors for whom English is not the working language are encouraged to consider using a professional language-editing service before submitting their manuscripts.