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钯催化的（香豆素基）甲基乙酸酯与 C、N 和 S 亲核试剂的取代反应。

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles.

机构信息

Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7528, USA ; KU Chemical Methodologies and Library Development Center of Excellence, University of Kansas, 1501 Wakarusa Drive, Lawrence, Kansas 66047, USA.

出版信息

Beilstein J Org Chem. 2012;8:1200-7. doi: 10.3762/bjoc.8.133. Epub 2012 Jul 27.

DOI:10.3762/bjoc.8.133
PMID:23019448
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3458738/
Abstract

The palladium-catalyzed nucleophilic substitution of (coumarinyl)methyl acetates is described. The reaction proceeds though a palladium π-benzyl-like complex and allows for many different types of C-, N-, and S-nucleophiles to be regioselectively added to the biologically active coumarin motif. This new method was utilized to prepare a 128-membered library of aminated coumarins for biological screening.

摘要

描述了（香豆素基）甲基乙酸酯的钯催化亲核取代反应。该反应通过钯π-苄基类似物进行，并允许许多不同类型的 C、N 和 S 亲核试剂选择性地添加到生物活性香豆素基序中。该新方法用于制备 128 个成员的胺化香豆素文库，用于生物学筛选。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/73570dfda2eb/Beilstein_J_Org_Chem-08-1200-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/cafd59a3d70d/Beilstein_J_Org_Chem-08-1200-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/52eb11a16e8e/Beilstein_J_Org_Chem-08-1200-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/95800921bb82/Beilstein_J_Org_Chem-08-1200-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/51a1d83e36e0/Beilstein_J_Org_Chem-08-1200-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/5db13a2d8707/Beilstein_J_Org_Chem-08-1200-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/9ece491df6d7/Beilstein_J_Org_Chem-08-1200-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/791dc4a376fe/Beilstein_J_Org_Chem-08-1200-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/075d227e2a05/Beilstein_J_Org_Chem-08-1200-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/73570dfda2eb/Beilstein_J_Org_Chem-08-1200-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/cafd59a3d70d/Beilstein_J_Org_Chem-08-1200-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/52eb11a16e8e/Beilstein_J_Org_Chem-08-1200-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/95800921bb82/Beilstein_J_Org_Chem-08-1200-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/51a1d83e36e0/Beilstein_J_Org_Chem-08-1200-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/5db13a2d8707/Beilstein_J_Org_Chem-08-1200-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/9ece491df6d7/Beilstein_J_Org_Chem-08-1200-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/791dc4a376fe/Beilstein_J_Org_Chem-08-1200-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/075d227e2a05/Beilstein_J_Org_Chem-08-1200-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2923/3458738/73570dfda2eb/Beilstein_J_Org_Chem-08-1200-g004.jpg

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Decarboxylative benzylation and arylation of nitriles.腈的脱羧苄基化和芳基化。
Chem Commun (Camb). 2012 Jan 4;48(1):142-4. doi: 10.1039/c1cc16011g. Epub 2011 Nov 7.
4
Migratory decarboxylative coupling of coumarins: synthetic and mechanistic aspects.香豆素的迁移脱羧偶联反应：合成及机理研究
Angew Chem Int Ed Engl. 2011 May 23;50(22):5157-61. doi: 10.1002/anie.201100765. Epub 2011 Apr 19.
5
Design, synthesis, and biological evaluation of imidazolyl derivatives of 4,7-disubstituted coumarins as aromatase inhibitors selective over 17-α-hydroxylase/C17-20 lyase.设计、合成和 4,7-二取代香豆素的咪唑衍生物作为芳香酶抑制剂的生物评价，其对 17-α-羟化酶/C17-20 裂解酶具有选择性。
J Med Chem. 2011 Mar 24;54(6):1613-25. doi: 10.1021/jm101120u. Epub 2011 Feb 22.
6
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Chem Commun (Camb). 2011 Mar 7;47(9):2679-81. doi: 10.1039/c0cc05160h. Epub 2011 Jan 31.
7
Transition metal-catalyzed decarboxylative allylation and benzylation reactions.过渡金属催化脱羧烯丙基化和苄基化反应。
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8
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9
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