• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

钯催化酰基硅烷与炔烃的加成反应：C-Si键的活化

Palladium-catalyzed addition of acylsilanes across alkynes the activation of a C-Si bond.

作者信息

Inagaki Tetsuya, Ando Takahiro, Sakurai Shun, Yamanaka Masahiro, Tobisu Mamoru

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University Suita 565-0871 Osaka Japan

Department of Chemistry and Research Center for Smart Molecules, Faculty of Science, Rikkyo University Nishi-Ikebukuro, Toshima-ku Tokyo 171-8501 Japan

出版信息

Chem Sci. 2023 Feb 13;14(10):2706-2712. doi: 10.1039/d3sc00181d. eCollection 2023 Mar 8.

DOI:10.1039/d3sc00181d
PMID:36908943
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9993849/
Abstract

Palladium-catalyzed addition of a C-Si bond in acylsilanes across the triple bonds in an alkyne bearing a carbonyl group at one terminal is reported. The reaction proceeds with excellent regioselectivity, in which a silyl group is incorporated into the carbon α to the carbonyl group, allowing for straightforward access to a variety of functionalized alkenylsilane derivatives. Catalytic synthesis of indanones by annulation between acylsilanes and alkynes with an identical catalytic system is also reported.

摘要

据报道，钯催化酰基硅烷中的碳 - 硅键加成到一端带有羰基的炔烃的三键上。该反应具有出色的区域选择性，其中硅烷基被引入到羰基的α-碳上，从而可以直接获得各种功能化的烯基硅烷衍生物。还报道了使用相同催化体系通过酰基硅烷和炔烃之间的环化反应催化合成茚满酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/9b336da15ebc/d3sc00181d-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/c13e4dcd8af3/d3sc00181d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/9a21b998b9c0/d3sc00181d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/986896c8e64f/d3sc00181d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/291a56bd8507/d3sc00181d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/31674b70f3c4/d3sc00181d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/faa826b63805/d3sc00181d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/9b336da15ebc/d3sc00181d-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/c13e4dcd8af3/d3sc00181d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/9a21b998b9c0/d3sc00181d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/986896c8e64f/d3sc00181d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/291a56bd8507/d3sc00181d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/31674b70f3c4/d3sc00181d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/faa826b63805/d3sc00181d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab02/9993849/9b336da15ebc/d3sc00181d-f7.jpg

相似文献

1
Palladium-catalyzed addition of acylsilanes across alkynes the activation of a C-Si bond.钯催化酰基硅烷与炔烃的加成反应：C-Si键的活化
Chem Sci. 2023 Feb 13;14(10):2706-2712. doi: 10.1039/d3sc00181d. eCollection 2023 Mar 8.
2
Palladium-Catalyzed Silylacylation of Allenes Using Acylsilanes.使用酰基硅烷的钯催化丙二烯的硅酰化反应
Angew Chem Int Ed Engl. 2022 May 16;61(21):e202202387. doi: 10.1002/anie.202202387. Epub 2022 Mar 23.
3
Gold(I)-Catalyzed Addition of Silylacetylenes to Acylsilanes: Synthesis of Indanones by C-H Functionalization through a Gold(I) Carbenoid.金（I）催化的硅基炔与酰基硅烷加成反应：通过金（I）卡宾中间体的 C-H 功能化合成茚酮。
Angew Chem Int Ed Engl. 2015 Nov 9;54(46):13678-81. doi: 10.1002/anie.201505830. Epub 2015 Sep 21.
4
Palladium-catalyzed carbonylative annulation of internal alkynes: synthesis of 3,4-disubstituted coumarins.钯催化内炔的羰基化环化反应：3,4-二取代香豆素的合成
J Org Chem. 2003 Nov 28;68(24):9423-32. doi: 10.1021/jo0350763.
5
Palladium-Catalyzed Addition of Trifluoroacetylsilanes to Alkenes and Allenes via the Cleavage of C-Si Bonds.钯催化三氟乙酰硅烷通过碳-硅键裂解加成到烯烃和丙二烯上。
Org Lett. 2024 Mar 15;26(10):2141-2145. doi: 10.1021/acs.orglett.4c00595. Epub 2024 Mar 5.
6
Controllable Si-C Bond Activation Enables Stereocontrol in the Palladium-Catalyzed [4+2] Annulation of Cyclopropenes with Benzosilacyclobutanes.可控的硅-碳键活化实现了钯催化环丙烯与苯并硅杂环丁烷的[4+2]环化反应中的立体控制。
Angew Chem Int Ed Engl. 2020 Jan 7;59(2):790-797. doi: 10.1002/anie.201913060. Epub 2019 Dec 12.
7
Palladium-Catalyzed Benzannulations of 1-(Indol-2-yl)but-3-yn-1-ols: Easy Access to Functionalized Carbazoles.钯催化的1-(吲哚-2-基)丁-3-炔-1-醇的苯并环化反应：便捷合成官能化咔唑
Org Lett. 2022 Mar 18;24(10):1895-1900. doi: 10.1021/acs.orglett.2c00182. Epub 2022 Mar 7.
8
Silver-Catalyzed Activation of Terminal Alkynes for Synthesizing Nitrogen-Containing Molecules.银催化末端炔烃的活化用于合成含氮分子。
Acc Chem Res. 2020 Mar 17;53(3):662-675. doi: 10.1021/acs.accounts.9b00623. Epub 2020 Feb 20.
9
Synthesis of annulated gamma-carbolines and heteropolycycles by the palladium-catalyzed intramolecular annulation of alkynes.通过钯催化的炔烃分子内环化反应合成稠环γ-咔啉和杂环化合物。
J Org Chem. 2003 Jun 27;68(13):5132-8. doi: 10.1021/jo0343228.
10
Carbopalladation of nitriles: synthesis of 3,4-disubstituted 2-aminonaphthalenes and 1,3-benzoxazine derivatives by the palladium-catalyzed annulation of alkynes by (2-Iodophenyl)acetonitrile.腈的碳钯化反应：通过钯催化（2-碘苯基）乙腈与炔烃的环化反应合成3,4-二取代的2-氨基萘和1,3-苯并恶嗪衍生物。
J Org Chem. 2003 Jan 24;68(2):339-47. doi: 10.1021/jo026229+.

引用本文的文献

1
Benzocyclobutenone synthesis exploiting acylsilanes as photofunctional directing groups.利用酰基硅烷作为光功能导向基团的苯并环丁烯酮合成。
Chem Sci. 2024 Oct 25;15(46):19328-35. doi: 10.1039/d4sc05715e.
2
Bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl-ene reaction for construction of 5-oxazoylmethyl α-silyl alcohol.双金属串联催化实现的对映选择性环异构化/羰基-烯反应用于构建5-恶唑基甲基α-硅醇。
Chem Sci. 2023 Jul 7;14(31):8315-8320. doi: 10.1039/d3sc01048a. eCollection 2023 Aug 9.

本文引用的文献

1
Light-Promoted Arylsilylation of Alkenes with Hydrosilanes.光促进的烯烃与硅烷的芳基硅基化反应。
Org Lett. 2022 Oct 7;24(39):7145-7150. doi: 10.1021/acs.orglett.2c02835. Epub 2022 Sep 22.
2
Three-Component Ni-Catalyzed Silylacylation of Alkenes.镍催化的烯烃三组分硅酰化反应
ACS Catal. 2021 Feb 5;11(3):1858-1862. doi: 10.1021/acscatal.0c05449. Epub 2021 Jan 26.
3
Palladium-Catalyzed Silylacylation of Allenes Using Acylsilanes.使用酰基硅烷的钯催化丙二烯的硅酰化反应
Angew Chem Int Ed Engl. 2022 May 16;61(21):e202202387. doi: 10.1002/anie.202202387. Epub 2022 Mar 23.
4
Salt-Stabilized Silylzinc Pivalates for Nickel-Catalyzed Carbosilylation of Alkenes.用于镍催化烯烃碳硅化反应的盐稳定新戊酸硅锌盐
Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202202379. doi: 10.1002/anie.202202379. Epub 2022 Feb 28.
5
Palladium-Catalyzed Silylcyanation of Ynamides: Regio- and Stereoselective Access to Tetrasubstituted 3-Silyl-2-Aminoacrylonitriles.钯催化的烯酰胺硅氰化反应：区域和立体选择性合成四取代的3-硅基-2-氨基丙烯腈
Angew Chem Int Ed Engl. 2022 Mar 28;61(14):e202200204. doi: 10.1002/anie.202200204. Epub 2022 Feb 2.
6
Palladium-Catalyzed Siloxycyclopropanation of Alkenes Using Acylsilanes.使用酰基硅烷通过钯催化的烯烃硅氧基环丙烷化反应
J Am Chem Soc. 2022 Jan 26;144(3):1099-1105. doi: 10.1021/jacs.1c11497. Epub 2022 Jan 12.
7
Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction.钯/铜共催化内炔与酰氟和硅硼烷的芳基硅基化反应：通过三组分偶联反应合成四取代烯基硅烷
Org Lett. 2022 Jan 14;24(1):385-389. doi: 10.1021/acs.orglett.1c04060. Epub 2021 Dec 22.
8
Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts.催化硅氢化反应的最新进展：超越传统铂催化剂的发展
Angew Chem Int Ed Engl. 2021 Jan 11;60(2):550-565. doi: 10.1002/anie.202008729. Epub 2020 Dec 1.
9
Nazarov reaction: current trends and recent advances in the synthesis of natural compounds and their analogs.纳扎罗夫反应：天然化合物及其类似物合成的当前趋势与最新进展
Org Biomol Chem. 2017 Oct 11;15(39):8245-8269. doi: 10.1039/c7ob01981e.
10
Iron-Catalyzed anti-Selective Carbosilylation of Internal Alkynes.铁催化的炔烃反选择性硅碳加成反应。
Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13298-13301. doi: 10.1002/anie.201706333. Epub 2017 Sep 19.