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高化学选择性的苯酚合成。

High chemoselectivity in the phenol synthesis.

机构信息

Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

出版信息

Beilstein J Org Chem. 2011;7:794-801. doi: 10.3762/bjoc.7.90. Epub 2011 Jun 10.

DOI:10.3762/bjoc.7.90
PMID:21804874
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3135103/
Abstract

Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of the gold-catalyzed phenol synthesis are much faster than the steps of the interception reaction. In the latter the barrier of activation is higher. At the same time this explains the high tolerance of this very efficient and general reaction towards functional groups.

摘要

试图捕获金催化苯酚合成的早期中间体失败了。无论是烯丙基、酮基还是醇基，都不能拦截金卡宾物种。这表明金催化苯酚合成的竞争步骤比拦截反应的步骤快得多。在后一种情况下，活化能垒更高。同时，这也解释了这种非常高效和通用的反应对官能团具有高耐受性的原因。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/5010fed9e3b8/Beilstein_J_Org_Chem-07-794-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/dc57c32a5a28/Beilstein_J_Org_Chem-07-794-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/c6187995675d/Beilstein_J_Org_Chem-07-794-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/5f5e232d13a5/Beilstein_J_Org_Chem-07-794-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/7e21e591b878/Beilstein_J_Org_Chem-07-794-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/fd62ec24e3cb/Beilstein_J_Org_Chem-07-794-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/1bee58529c64/Beilstein_J_Org_Chem-07-794-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/9fa746102511/Beilstein_J_Org_Chem-07-794-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/1c4bdfd524f5/Beilstein_J_Org_Chem-07-794-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/08ac47823a25/Beilstein_J_Org_Chem-07-794-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/0e58e8de7b2b/Beilstein_J_Org_Chem-07-794-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/8c6546a93daa/Beilstein_J_Org_Chem-07-794-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/c09ebdac3967/Beilstein_J_Org_Chem-07-794-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/268b62101582/Beilstein_J_Org_Chem-07-794-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/e622b33b22aa/Beilstein_J_Org_Chem-07-794-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/d3d693dce8d6/Beilstein_J_Org_Chem-07-794-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/d43d8854fc9e/Beilstein_J_Org_Chem-07-794-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/5010fed9e3b8/Beilstein_J_Org_Chem-07-794-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/dc57c32a5a28/Beilstein_J_Org_Chem-07-794-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/c6187995675d/Beilstein_J_Org_Chem-07-794-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/5f5e232d13a5/Beilstein_J_Org_Chem-07-794-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/7e21e591b878/Beilstein_J_Org_Chem-07-794-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/fd62ec24e3cb/Beilstein_J_Org_Chem-07-794-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/1bee58529c64/Beilstein_J_Org_Chem-07-794-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/9fa746102511/Beilstein_J_Org_Chem-07-794-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/1c4bdfd524f5/Beilstein_J_Org_Chem-07-794-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/08ac47823a25/Beilstein_J_Org_Chem-07-794-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/0e58e8de7b2b/Beilstein_J_Org_Chem-07-794-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/8c6546a93daa/Beilstein_J_Org_Chem-07-794-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/c09ebdac3967/Beilstein_J_Org_Chem-07-794-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/268b62101582/Beilstein_J_Org_Chem-07-794-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/e622b33b22aa/Beilstein_J_Org_Chem-07-794-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/d3d693dce8d6/Beilstein_J_Org_Chem-07-794-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/d43d8854fc9e/Beilstein_J_Org_Chem-07-794-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5494/3135103/5010fed9e3b8/Beilstein_J_Org_Chem-07-794-g018.jpg

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本文引用的文献

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Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.铜、银和金催化的迁移环异构化反应合成杂环五元环。
Aldrichimica Acta. 2010;43(2):37-46.
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Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles.金催化功能化丙二烯的亲核环化反应：构建碳环和杂环的有效方法
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Gold and platinum catalysis--a convenient tool for generating molecular complexity.
金（I）或三氯化镓催化炔烃的氢芳基化合成荧蒽。
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金和铂催化——生成分子复杂性的便捷工具。
Chem Soc Rev. 2009 Nov;38(11):3208-21. doi: 10.1039/b816696j. Epub 2009 Jul 22.
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Gold catalysis in total synthesis.全合成中的金催化
Chem Soc Rev. 2008 Sep;37(9):1766-75. doi: 10.1039/b615629k. Epub 2008 Jul 7.
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Alternative synthetic methods through new developments in catalysis by gold.通过金催化的新进展实现的替代合成方法。
Chem Rev. 2008 Aug;108(8):3266-325. doi: 10.1021/cr068435d. Epub 2008 Jul 24.
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Gold-catalyzed organic transformations.金催化的有机转化反应。
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Gold catalysis: deuterated substrates as the key for an experimental insight into the mechanism and selectivity of the phenol synthesis.
Chemistry. 2008;14(12):3703-8. doi: 10.1002/chem.200701795.
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Relativistic effects in homogeneous gold catalysis.均相金催化中的相对论效应。
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Molecular diversity through gold catalysis with alkynes.通过金催化炔烃实现分子多样性
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