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钯催化的烯烃与芳基膦酰胺的 -Alkenylation。

Palladium-Catalyzed -Alkenylation of -Aryl Phosphoramidates with Alkenes.

机构信息

Department of Orthopaedics Surgery, The Second Affiliated Hospital and Yuying Children's Hospital of Wenzhou Medical University, Wenzhou 325000, China.

School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325015, China.

出版信息

Molecules. 2023 May 31;28(11):4466. doi: 10.3390/molecules28114466.

DOI:10.3390/molecules28114466
PMID:37298944
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10254562/
Abstract

Versatile and concise Pd-catalyzed oxidative -alkenylation of -aryl phosphoramidates with alkenes is described in this study, a reaction that is of great significance but surprisingly unexploited. The transformation proceeds under mild reaction conditions, using O as a green oxidant and TBAB as an effective additive. An efficient catalytic system allows a variety of drug-related substrates to participate in these transformations, which is of great interest in the drug discovery and development of phosphoramidates.

摘要

本研究中描述了一种多功能且简洁的 Pd 催化的芳基膦酰胺与烯烃的氧化-烯丙基化反应,该反应具有重要意义,但令人惊讶的是尚未得到充分利用。该转化在温和的反应条件下进行,使用 O 作为绿色氧化剂和 TBAB 作为有效添加剂。一个高效的催化体系允许各种与药物相关的底物参与这些转化,这对于药物发现和磷酰胺的开发具有重要意义。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/0f8fadabc983/molecules-28-04466-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/293e4b25d7ff/molecules-28-04466-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/045b4488a7af/molecules-28-04466-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/966e5e03f588/molecules-28-04466-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/0f8a40d4e564/molecules-28-04466-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/0f8fadabc983/molecules-28-04466-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/293e4b25d7ff/molecules-28-04466-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/045b4488a7af/molecules-28-04466-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/966e5e03f588/molecules-28-04466-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/0f8a40d4e564/molecules-28-04466-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c385/10254562/0f8fadabc983/molecules-28-04466-sch005.jpg

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本文引用的文献

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Org Biomol Chem. 2023 Apr 12;21(15):3101-3104. doi: 10.1039/d3ob00296a.
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I-mediated coupling of quinazolinone enamines with 2-aminopyridines: a new strategy to access spiroquinazolinones.I 介导的喹唑啉酮烯胺与 2-氨基吡啶的偶联:一种构建螺环喹唑啉酮的新策略。
Org Biomol Chem. 2023 Mar 15;21(11):2355-2360. doi: 10.1039/d3ob00083d.
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Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles.
钯催化的α-烯烃与吲哚的氧化胺化反应。
Org Lett. 2022 Aug 12;24(31):5746-5750. doi: 10.1021/acs.orglett.2c02190. Epub 2022 Jul 29.
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Recent advances in the synthesis and applications of phosphoramides.膦酰胺的合成及应用研究进展。
Org Biomol Chem. 2021 Dec 8;19(47):10296-10313. doi: 10.1039/d1ob01566d.
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Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.高区域和非对映选择性键合的氮杂-Wacker 环化反应的烯基膦酰胺酯。
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