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涉及锌基硅亲核试剂1,4-加成的甲硅烷基化环丁酮和环丁烯衍生物的合成

Synthesis of Silylated Cyclobutanone and Cyclobutene Derivatives Involving 1,4-Addition of Zinc-Based Silicon Nucleophiles.

作者信息

Cui Ming, Oestreich Martin

机构信息

Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany.

出版信息

Chemistry. 2021 Nov 22;27(65):16103-16106. doi: 10.1002/chem.202102993. Epub 2021 Oct 7.

DOI:10.1002/chem.202102993
PMID:34490934
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9292915/
Abstract

A copper-catalyzed conjugate silylation of various cyclobutenone derivatives with Me PhSiZnCl ⋅ 2LiCl or (Me PhSi) Zn ⋅ xLiCl (x≤4) to generate β-silylated cyclobutanones is reported. Trapping the intermediate enolate with ClP(O)(OPh) affords silylated enol phosphates that can be further engaged in Kumada cross-coupling reactions to yield silylated cyclobutene derivatives.

摘要

据报道，通过铜催化各种环丁烯酮衍生物与MePhSiZnCl·2LiCl或(MePhSi)Zn·xLiCl（x≤4）进行共轭硅氢化反应，生成β-硅烷基化环丁酮。用ClP(O)(OPh)捕获中间体烯醇盐，可得到硅烷基化烯醇磷酸酯，其可进一步参与 Kumada 交叉偶联反应，生成硅烷基化环丁烯衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/a9c1d7553093/CHEM-27-16103-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/81434d29a0c0/CHEM-27-16103-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/45b954cf81c9/CHEM-27-16103-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/f3a70ca9da4c/CHEM-27-16103-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/a9c1d7553093/CHEM-27-16103-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/81434d29a0c0/CHEM-27-16103-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/45b954cf81c9/CHEM-27-16103-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/f3a70ca9da4c/CHEM-27-16103-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8c4d/9292915/a9c1d7553093/CHEM-27-16103-g007.jpg

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