区域选择性铜催化的内芳基炔烃的硅氢化反应
Regioselective Cu-Catalyzed Hydrosilylation of Internal Aryl Alkynes.
作者信息
Sloane Samantha E, Sancheti Shashank P, Hendy Moataz S, Smith Kathryn M, Thorat Raviraj Ananda, Senkum Hathaithep, Clark Joseph R
机构信息
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53233, United States.
Department of Chemistry, University of Tennessee, Knoxville, Knoxville, Tennessee 37996, United States.
出版信息
Org Lett. 2025 Feb 14;27(6):1412-1416. doi: 10.1021/acs.orglett.4c04722. Epub 2025 Jan 30.
Abstract
Construction of vinylsilane building blocks is important for advancing the synthesis of complex small molecules and natural products. Herein, we report a highly regio- and stereoselective copper-catalyzed hydrosilylation of unsymmetrical internal aryl alkynes. The reaction is performed across a broad scope of internal aryl alkynes, providing exclusive access to α-vinylsilane alkenyl arene products, including several silylated small molecule drug analogs.
摘要
乙烯基硅烷结构单元的构建对于推进复杂小分子和天然产物的合成至关重要。在此，我们报道了一种高度区域和立体选择性的铜催化不对称内芳基炔烃的硅氢化反应。该反应适用于多种内芳基炔烃，可专一性地得到α-乙烯基硅烷烯基芳烃产物，包括几种硅烷化的小分子药物类似物。
相似文献
1
Regioselective Cu-Catalyzed Hydrosilylation of Internal Aryl Alkynes.区域选择性铜催化的内芳基炔烃的硅氢化反应
Org Lett. 2025 Feb 14;27(6):1412-1416. doi: 10.1021/acs.orglett.4c04722. Epub 2025 Jan 30.
2
Cationic-palladium catalyzed regio- and stereoselective syn-1,2-dicarbofunctionalization of unsymmetrical internal alkynes.阳离子钯催化的非对称内炔烃的区域和立体选择性顺式 1,2-双官能团化。
Nat Commun. 2022 Mar 16;13(1):1360. doi: 10.1038/s41467-022-28949-7.
3
Xantphos Doped POPs-PPh as Heterogeneous Ligand for Cobalt-Catalyzed Highly Regio- and Stereoselective Hydrosilylation of Alkynes.掺杂 Xantphos 的 POPs-PPh 作为均相配体用于钴催化炔烃的高区域和立体选择性氢化硅烷化反应。
Chem Asian J. 2019 Jan 4;14(1):149-154. doi: 10.1002/asia.201801241. Epub 2018 Nov 28.
4
Heteroatom-Assisted Regio- and Stereoselective Hydrosilylation of Unsymmetric Internal Alkynes by Scandium Catalyst.钪催化剂介导的不对称内炔烃的杂原子辅助区域和立体选择性硅氢化反应
Angew Chem Int Ed Engl. 2025 Apr 17;64(17):e202502665. doi: 10.1002/anie.202502665. Epub 2025 Feb 28.
5
Highly Regioselective Cobalt-Catalyzed Hydroboration of Internal Alkynes.钴催化内炔烃的高度区域选择性硼氢化反应
Angew Chem Int Ed Engl. 2022 Sep 5;61(36):e202208473. doi: 10.1002/anie.202208473. Epub 2022 Jul 29.
6
Regio- and Stereoselective Hydrosilylation of Unsymmetrical Alkynes Catalyzed by a Well-Defined, Low-Valent Cobalt Catalyst.区域和立体选择性氢化不对称炔烃的定义明确、低价钴催化剂的催化作用。
Org Lett. 2016 Sep 2;18(17):4242-5. doi: 10.1021/acs.orglett.6b01987. Epub 2016 Aug 23.
7
Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.阳离子钌配合物催化的炔烃硅氢化反应：高效且通用的反式加成。
J Am Chem Soc. 2005 Dec 21;127(50):17644-55. doi: 10.1021/ja0528580.
8
Palladium-Catalyzed Regio- and Stereoselective Hydroaminocarbonylation of Unsymmetrical Internal Alkynes toward α,β-Unsaturated Amides.钯催化不对称内炔烃区域和立体选择性氢氨羰基化反应合成α,β-不饱和酰胺
Org Lett. 2022 Jun 24;24(24):4464-4469. doi: 10.1021/acs.orglett.2c01693. Epub 2022 Jun 12.
9
Highly Chemo-, Regio-, and Stereoselective Cobalt-Catalyzed Markovnikov Hydrosilylation of Alkynes.高度选择性钴催化炔烃 Markovnikov 氢硅烷化反应。
Angew Chem Int Ed Engl. 2016 Aug 26;55(36):10835-8. doi: 10.1002/anie.201605501. Epub 2016 Jul 21.
10
Regio- and stereoselective hydrosilylation of alkynes catalyzed by three-coordinate cobalt(I) alkyl and silyl complexes.三配位钴（I）烷基和硅基配合物催化炔烃的区域和立体选择性氢化硅烷化反应。
J Am Chem Soc. 2014 Dec 17;136(50):17414-7. doi: 10.1021/ja510924v. Epub 2014 Dec 9.
本文引用的文献
1
Precision Deuteration Using Cu-Catalyzed Transfer Hydrodeuteration to Access Small Molecules Deuterated at the Benzylic Position.使用铜催化的转移氢氘化反应实现苄基位置氘代的小分子的精准氘代。
JACS Au. 2023 May 17;3(6):1583-1589. doi: 10.1021/jacsau.3c00053. eCollection 2023 Jun 26.
2
Design, Synthesis, and Structure-Activity Relationships of Biaryl Anilines as Subtype-Selective PPAR-alpha Agonists.作为亚型选择性PPAR-α激动剂的联芳基苯胺类化合物的设计、合成及构效关系
ACS Med Chem Lett. 2023 May 23;14(6):766-776. doi: 10.1021/acsmedchemlett.3c00056. eCollection 2023 Jun 8.
3
Deuterium in drug discovery: progress, opportunities and challenges.药物发现中的氘代：进展、机遇与挑战。
Nat Rev Drug Discov. 2023 Jul;22(7):562-584. doi: 10.1038/s41573-023-00703-8. Epub 2023 Jun 5.
4
One-Metal/Two-Ligand for Dual Activation Tandem Catalysis: Photoinduced Cu-Catalyzed Anti-hydroboration of Alkynes.一金属/双配体双重激活串联催化：光诱导 Cu 催化炔烃反硼氢化反应。
J Am Chem Soc. 2022 Jul 20;144(28):13006-13017. doi: 10.1021/jacs.2c05805. Epub 2022 Jul 5.
5
Enantioselective Synthesis of Enantioisotopomers with Quantitative Chiral Analysis by Chiral Tag Rotational Spectroscopy.对映异构体的对映体分馏物的对映选择性合成及手性标签旋转光谱的定量手性分析。
Angew Chem Int Ed Engl. 2022 Aug 15;61(33):e202207275. doi: 10.1002/anie.202207275. Epub 2022 Jul 8.
6
Regio-selective and stereo-selective hydrosilylation of internal alkynes catalyzed by ruthenium complexes.钌配合物催化的内炔烃的区域选择性和立体选择性硅氢化反应
RSC Adv. 2018 Aug 7;8(49):28261-28265. doi: 10.1039/c8ra04083d. eCollection 2018 Aug 2.
7
Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes*.环状（烷基）（氨基）卡宾配体实现铜催化末端炔烃的 Markovnikov 硼化和硅化反应：一种多功能构建官能化烯烃的途径*。
Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19871-19878. doi: 10.1002/anie.202106107. Epub 2021 Jul 29.
8
Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy.铜催化的芳基烯烃转移加氢氘化反应，通过分子旋转共振光谱法进行定量同位素纯度分析。
J Am Chem Soc. 2021 May 26;143(20):7707-7718. doi: 10.1021/jacs.1c00884. Epub 2021 May 17.
9
Schiff Base Cobalt(II) Complex-Catalyzed Highly Markovnikov-Selective Hydrosilylation of Alkynes.席夫碱钴（II）配合物催化的炔烃的高度马氏选择性硅氢化反应
Org Lett. 2021 Feb 5;23(3):663-667. doi: 10.1021/acs.orglett.0c03721. Epub 2021 Jan 13.
10
Copper-Catalyzed -Markovnikov Hydrosilylation of Terminal Alkynes.铜催化末端炔烃的马氏硅氢化反应
Org Lett. 2020 Oct 2;22(19):7735-7742. doi: 10.1021/acs.orglett.0c02952. Epub 2020 Sep 23.
Zotero 插件