光诱导钴肟催化双环[1.1.0]丁烷的区域和非对映选择性析氢C(sp3) - h磷酸化

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-15 DOI:10.1021/acs.orglett.4c04702

Peng-Fei Chen, Meng-Yuan Dong, Chun-Yu Han, Dong-Sheng Li, Yang Hong, Fei Xue, Fang Liu, Hong-Ping Deng

{"title":"光诱导钴肟催化双环[1.1.0]丁烷的区域和非对映选择性析氢C(sp3) - h磷酸化","authors":"Peng-Fei Chen, Meng-Yuan Dong, Chun-Yu Han, Dong-Sheng Li, Yang Hong, Fei Xue, Fang Liu, Hong-Ping Deng","doi":"10.1021/acs.orglett.4c04702","DOIUrl":null,"url":null,"abstract":"Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)–H functionalization at the C2 position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of C2 C(sp3)–H phosphorylation with BCBs enabled by photoinduced cobaloxime catalysis was realized in a regio- and diastereoselective manner. This oxidant- and additional photocatalyst-free method enabled C(sp3)–H phosphorylation with a wide range of BCBs and diarylphosphine oxides. The mechanism was studied via control experiments and DFT calculation. Moreover, the efficiency of this approach was highlighted in the synthesis of high-value, structurally complex molecules.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes\",\"authors\":\"Peng-Fei Chen, Meng-Yuan Dong, Chun-Yu Han, Dong-Sheng Li, Yang Hong, Fei Xue, Fang Liu, Hong-Ping Deng\",\"doi\":\"10.1021/acs.orglett.4c04702\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp3)–H functionalization at the C2 position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of C2 C(sp3)–H phosphorylation with BCBs enabled by photoinduced cobaloxime catalysis was realized in a regio- and diastereoselective manner. This oxidant- and additional photocatalyst-free method enabled C(sp3)–H phosphorylation with a wide range of BCBs and diarylphosphine oxides. The mechanism was studied via control experiments and DFT calculation. Moreover, the efficiency of this approach was highlighted in the synthesis of high-value, structurally complex molecules.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"24 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2025-01-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c04702\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04702","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

自由基引发的双环[1.1.0]丁烷功能化（BCBs）是获得各种环丁烷衍生物的直接方法。然而，在bcb的C2位置上选择性的C(sp3) -H功能化仍然很少。本文以区域选择性和非对映选择性的方式实现了C2 C(sp3) - h磷酸化与光诱导钴胺肟催化的bcb的温和析氢方案。这种无氧化剂和附加光催化剂的方法使C(sp3) - h与广泛的bcb和二芳基膦氧化物发生磷酸化。通过控制实验和DFT计算对其机理进行了研究。此外，这种方法的效率在合成高价值、结构复杂的分子方面得到了突出的体现。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes

查看原文本刊更多论文

Photoinduced Cobaloxime-Catalyzed Regio- and Diastereoselective Hydrogen-Evolution C(sp3)–H Phosphorylation of Bicyclo[1.1.0]butanes

Radical-initiated functionalization of bicyclo[1.1.0]butanes (BCBs) is a straightforward approach to accessing diverse cyclobutane derivatives. However, selective C(sp³)–H functionalization at the C2 position of BCBs remains scarce. Herein, a mild protocol for the hydrogen-evolution of C2 C(sp³)–H phosphorylation with BCBs enabled by photoinduced cobaloxime catalysis was realized in a regio- and diastereoselective manner. This oxidant- and additional photocatalyst-free method enabled C(sp³)–H phosphorylation with a wide range of BCBs and diarylphosphine oxides. The mechanism was studied via control experiments and DFT calculation. Moreover, the efficiency of this approach was highlighted in the synthesis of high-value, structurally complex molecules.

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

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.