[Ni(PnBu3)2Cl2]作为经济预催化剂用于芳基磺酸酯与卤化物的Suzuki-Miyaura交叉偶联反应

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-06-24 DOI:10.1016/j.tetlet.2025.155723

Eric Fortin Constant, Armaan Grewal, Eric C. Keske

{"title":"[Ni(PnBu3)2Cl2]作为经济预催化剂用于芳基磺酸酯与卤化物的Suzuki-Miyaura交叉偶联反应","authors":"Eric Fortin Constant, Armaan Grewal, Eric C. Keske","doi":"10.1016/j.tetlet.2025.155723","DOIUrl":null,"url":null,"abstract":"<div><div>The air stable precatalyst [Ni(PnBu<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] was successfully demonstrated to be highly active in the Suzuki-Miyaura reaction of aryl tosylates, mesylates and chlorides without the use of an external reducing agent. Biaryl products were typically formed in high yield without the requirement of large excesses of phenyl boronic acid derivatives or base. This precatalyst can be readily prepared from inexpensive starting materials representing a distinct economic advantage over previously reported precatalysts. We further report our computational studies indicating potential oxidative addition mechanisms with this precatalyst on aryl sulfonate electrophiles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"169 ","pages":"Article 155723"},"PeriodicalIF":1.5000,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides\",\"authors\":\"Eric Fortin Constant, Armaan Grewal, Eric C. Keske\",\"doi\":\"10.1016/j.tetlet.2025.155723\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The air stable precatalyst [Ni(PnBu<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] was successfully demonstrated to be highly active in the Suzuki-Miyaura reaction of aryl tosylates, mesylates and chlorides without the use of an external reducing agent. Biaryl products were typically formed in high yield without the requirement of large excesses of phenyl boronic acid derivatives or base. This precatalyst can be readily prepared from inexpensive starting materials representing a distinct economic advantage over previously reported precatalysts. We further report our computational studies indicating potential oxidative addition mechanisms with this precatalyst on aryl sulfonate electrophiles.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"169 \",\"pages\":\"Article 155723\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-06-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925002722\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925002722","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

空气稳定预催化剂[Ni(PnBu3)2Cl2]在不使用外部还原剂的情况下，成功地在芳基苯甲酸酯、甲磺酸酯和氯化物的Suzuki-Miyaura反应中表现出高活性。联芳基产品通常产率高，不需要大量过量的苯硼酸衍生物或碱。这种预催化剂可以很容易地从廉价的起始材料制备，与以前报道的预催化剂相比，具有明显的经济优势。我们进一步报告了我们的计算研究，表明该预催化剂对芳基磺酸盐亲电试剂的潜在氧化加成机制。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides

查看原文本刊更多论文

[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides

The air stable precatalyst [Ni(PnBu₃)₂Cl₂] was successfully demonstrated to be highly active in the Suzuki-Miyaura reaction of aryl tosylates, mesylates and chlorides without the use of an external reducing agent. Biaryl products were typically formed in high yield without the requirement of large excesses of phenyl boronic acid derivatives or base. This precatalyst can be readily prepared from inexpensive starting materials representing a distinct economic advantage over previously reported precatalysts. We further report our computational studies indicating potential oxidative addition mechanisms with this precatalyst on aryl sulfonate electrophiles.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.