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通过涉及环丁醇C-C键裂解的炔烃级联碳钯化/交叉烷基化反应合成苯并稠合杂环化合物。

Synthesis of Benzofused - and -Heterocycles through Cascade Carbopalladation/Cross-Alkylation of Alkynes Involving the C-C Cleavage of Cyclobutanols.

作者信息

Pérez-Gómez Marta, Herrera-Ramírez Piedad, Bautista Delia, Saura-Llamas Isabel, García-López José-Antonio

机构信息

Grupo de Química Organometálica, Departamento de Química Inorgánica, Facultad de Química, Universidad de Murcia, E-30100 Murcia, Spain.

ACTI, Universidad de Murcia, E-30100 Murcia, Spain.

出版信息

Organometallics. 2022 Mar 14;41(5):649-658. doi: 10.1021/acs.organomet.2c00015. Epub 2022 Mar 3.

DOI:10.1021/acs.organomet.2c00015
PMID:35308581
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8925021/
Abstract

We report a Pd-catalyzed route to heterocycles bearing a tetrasubstituted alkene fragment. Our approach merges the intramolecular carbopalladation of tethered alkynes with an alkylation step produced by the C-C cleavage of cyclobutanol derivatives. An alkenyl-Pd(II) intermediate has been isolated and characterized by X-ray diffraction studies. Interestingly, the nature of the tethering alkynyl chain influences the / stereochemistry of the alkenyl fragment in the functionalized heterocycles.

摘要

我们报道了一种通过钯催化合成带有四取代烯烃片段杂环化合物的方法。我们的方法是将 tethered 炔烃的分子内碳钯化反应与环丁醇衍生物的 C-C 裂解产生的烷基化步骤相结合。通过 X 射线衍射研究分离并表征了一种烯基钯（II）中间体。有趣的是，连接炔基链的性质会影响功能化杂环中烯基片段的 / 立体化学。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/8a8486771225/om2c00015_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/7f28b93d33e2/om2c00015_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/ee644a1db562/om2c00015_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/62bd9af2e5b6/om2c00015_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/4052d4678075/om2c00015_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/8a8486771225/om2c00015_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/7f28b93d33e2/om2c00015_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/ee644a1db562/om2c00015_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/62bd9af2e5b6/om2c00015_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/4052d4678075/om2c00015_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8d9c/8925021/8a8486771225/om2c00015_0010.jpg

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本文引用的文献

1
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Organometallics. 2021 Feb 22;40(4):539-556. doi: 10.1021/acs.organomet.0c00787. Epub 2021 Jan 29.
2
Palladium-Catalyzed Asymmetric Cross-Coupling Reactions of Cyclobutanols and Unactivated Olefins.钯催化环丁醇与未活化烯烃的不对称交叉偶联反应
Org Lett. 2021 Dec 17;23(24):9520-9525. doi: 10.1021/acs.orglett.1c03739. Epub 2021 Dec 1.
3
通过接力导向基团辅助的铑催化芳烃远程双官能化反应
Chem Sci. 2022 May 30;13(24):7347-7354. doi: 10.1039/d2sc02205b. eCollection 2022 Jun 22.
Palladium-Catalyzed -Carbosilylation of Alkynes to Access Isoquinolinone-Containing Exocyclic Vinylsilanes.
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Org Lett. 2021 Aug 6;23(15):5772-5776. doi: 10.1021/acs.orglett.1c01931. Epub 2021 Jul 14.
4
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Molecules. 2020 Dec 13;25(24):5900. doi: 10.3390/molecules25245900.
5
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6
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J Org Chem. 2020 Apr 3;85(7):4682-4694. doi: 10.1021/acs.joc.9b03397. Epub 2020 Mar 25.
10
Pd-catalyzed cascade reactions involving skipped dienes: from double carbopalladation to remote C-C cleavage.钯催化涉及跳跃双烯的串联反应：从双碳钯化到远程碳-碳裂解。
Chem Commun (Camb). 2019 Aug 22;55(69):10281-10284. doi: 10.1039/c9cc04817k.