• 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

钴催化炔烃的一锅法不对称双官能团化反应合成手性偕(硼硅基)烷烃

Cobalt-Catalyzed One-Pot Asymmetric Difunctionalization of Alkynes to Access Chiral gem-(Borylsilyl)alkanes.

作者信息

You Yang'en, Ge Shaozhong

机构信息

Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore, Singapore.

出版信息

Angew Chem Int Ed Engl. 2021 Sep 13;60(38):20684-20688. doi: 10.1002/anie.202107405. Epub 2021 Aug 11.

DOI:10.1002/anie.202107405
PMID:34223687
Abstract

Enantioselective cobalt-catalyzed one-pot hydrosilylation and hydroboration of terminal alkynes has been developed employing a cobalt catalyst generated from Co(acac) and (R,R)-Me-Ferrocelane. A variety of terminal alkynes undergo this asymmetric transformation, affording the corresponding gem-(borylsilyl)alkane products with high enantioselectivity (up to 98 % ee). This one-pot reaction combines (E)-selective hydrosilylation of alkynes and consecutive enantioselective hydroboration of (E)-vinylsilanes with one chiral cobalt catalyst. This protocol represents the most straightforward approach to access versatile chiral gem-(borylsilyl)alkanes from readily available alkynes with commercially available cobalt salt and chiral ligand.

摘要

利用由Co(acac)和(R,R)-Me-Ferrocelane生成的钴催化剂,开发了对映选择性钴催化的末端炔烃一锅法硅氢化和硼氢化反应。多种末端炔烃可进行这种不对称转化,以高对映选择性(高达98% ee)得到相应的偕(硼硅基)烷产物。该一锅法反应将炔烃的(E)-选择性硅氢化与(E)-乙烯基硅烷的连续对映选择性硼氢化结合在一种手性钴催化剂上。该方法是从易得的炔烃、市售钴盐和手性配体获得通用手性偕(硼硅基)烷的最直接途径。

相似文献

1
Cobalt-Catalyzed One-Pot Asymmetric Difunctionalization of Alkynes to Access Chiral gem-(Borylsilyl)alkanes.钴催化炔烃的一锅法不对称双官能团化反应合成手性偕(硼硅基)烷烃
Angew Chem Int Ed Engl. 2021 Sep 13;60(38):20684-20688. doi: 10.1002/anie.202107405. Epub 2021 Aug 11.
2
Regio- and Enantioselective Cobalt-Catalyzed Sequential Hydrosilylation/Hydrogenation of Terminal Alkynes.区域和对映选择性钴催化末端炔烃的顺序氢化/还原反应。
Angew Chem Int Ed Engl. 2017 Jan 9;56(2):615-618. doi: 10.1002/anie.201610121. Epub 2016 Nov 30.
3
Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.手性铜催化炔烃的对映选择性双硼氢化反应制备手性二硼烷基烷烃。
Nat Commun. 2022 Jun 20;13(1):3524. doi: 10.1038/s41467-022-31234-2.
4
Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates.对氟烷基取代烯烃的对映选择性钴催化氢硼化反应,以获得手性氟烷基硼酸酯。
J Am Chem Soc. 2022 Aug 24;144(33):15333-15338. doi: 10.1021/jacs.2c06488. Epub 2022 Aug 11.
5
Enantioselective Cobalt-Catalyzed Cascade Hydrosilylation and Hydroboration of Alkynes to Access Enantioenriched 1,1-Silylboryl Alkanes.对映选择性钴催化炔烃的串联氢硅烷化和硼氢化反应,以获得对映富集的 1,1-硅基硼烷。
J Am Chem Soc. 2021 Aug 25;143(33):13124-13134. doi: 10.1021/jacs.1c04248. Epub 2021 Aug 12.
6
Asymmetric Cobalt-Catalyzed Regioselective Hydrosilylation/Cyclization of 1,6-Enynes.不对称钴催化的1,6-烯炔的区域选择性硅氢化/环化反应
Angew Chem Int Ed Engl. 2021 May 17;60(21):12046-12052. doi: 10.1002/anie.202100775. Epub 2021 Apr 20.
7
Cu-Catalyzed Reductive gem-Difunctionalization of Terminal Alkynes via Hydrosilylation/Hydroamination Cascade: Concise Synthesis of α-Aminosilanes.铜催化末端炔烃的还原双官能化反应通过硅氢化/氨氢化级联反应:α-氨基硅烷的简洁合成。
Chemistry. 2020 Jul 17;26(40):8725-8728. doi: 10.1002/chem.202001799. Epub 2020 Jun 25.
8
Iron- and Cobalt-Catalyzed Asymmetric Hydrofunctionalization of Alkenes and Alkynes.铁和钴催化的烯烃和炔烃的不对称氢官能化反应。
Acc Chem Res. 2021 Jun 1;54(11):2701-2716. doi: 10.1021/acs.accounts.1c00212. Epub 2021 May 19.
9
Cobalt-Catalyzed Enantioselective Synthesis of Chiral gem-Bis(boryl)alkanes.钴催化的手性偕二(硼基)烷烃的对映选择性合成。
Angew Chem Int Ed Engl. 2018 Sep 24;57(39):12935-12939. doi: 10.1002/anie.201805705. Epub 2018 Aug 30.
10
Asymmetric Synthesis of Silicon-Stereogenic Vinylhydrosilanes by Cobalt-Catalyzed Regio- and Enantioselective Alkyne Hydrosilylation with Dihydrosilanes.通过钴催化二硅烷与炔烃的区域和对映选择性氢硅化反应不对称合成硅立体中心乙烯基氢硅烷
Angew Chem Int Ed Engl. 2018 May 22;57(21):6319-6323. doi: 10.1002/anie.201802806. Epub 2018 Apr 25.

引用本文的文献

1
Copper-catalyzed highly switchable defluoroborylation and hydrodefluorination of 1-(trifluoromethyl)alkynes.铜催化的1-(三氟甲基)炔烃的高度可切换脱氟硼化和加氢脱氟反应
Nat Commun. 2024 Aug 17;15(1):7079. doi: 10.1038/s41467-024-51519-y.
2
Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis.通过串联钴催化实现1,3-烯炔与丙烯酸酯的路径发散偶联。
Nat Commun. 2024 Apr 23;15(1):3427. doi: 10.1038/s41467-024-47719-1.
3
Tandem manganese catalysis for the chemo-, regio-, and stereoselective hydroboration of terminal alkynes: precatalyst activation as a key to enhanced chemoselectivity.
串联锰催化实现末端炔烃的化学、区域和立体选择性硼氢化反应:预催化剂活化是提高化学选择性的关键。
RSC Adv. 2024 Feb 13;14(8):5514-5523. doi: 10.1039/d3ra08747f. eCollection 2024 Feb 7.
4
Ligand-modulated nickel-catalyzed regioselective silylalkylation of alkenes.配体调控的镍催化烯烃区域选择性硅烷基化反应
Nat Commun. 2023 Nov 23;14(1):7670. doi: 10.1038/s41467-023-43642-z.
5
Facile preparation of organosilanes from benzylboronates and -diborylalkanes mediated by KOBu.在叔丁醇钾介导下,由硼酸苄酯和二硼基烷烃简便制备有机硅烷。
Chem Sci. 2023 Jun 13;14(26):7355-7360. doi: 10.1039/d3sc02461j. eCollection 2023 Jul 5.
6
Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes.镍催化未活化末端烯烃的1,1-氨基硼化反应
ACS Catal. 2023 Apr 10;13(8):5538-5543. doi: 10.1021/acscatal.3c00888. eCollection 2023 Apr 21.
7
Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes.光催化区域选择性硅氢化反应用于偕二硼硅烷和邻二硼硅烷的发散合成。
Nat Commun. 2023 May 2;14(1):2525. doi: 10.1038/s41467-023-38224-y.
8
Recent progress in the chemistry of β-aminoketones.β-氨基酮化学的最新进展。
RSC Adv. 2022 Aug 31;12(38):24681-24712. doi: 10.1039/d2ra03864a. eCollection 2022 Aug 30.
9
Asymmetric multifunctionalization of alkynes via photo-irradiated organocatalysis.通过光辐照有机催化实现炔烃的不对称多功能化
Sci Adv. 2022 Sep 16;8(37):eadd2574. doi: 10.1126/sciadv.add2574. Epub 2022 Sep 14.
10
Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates.对氟烷基取代烯烃的对映选择性钴催化氢硼化反应,以获得手性氟烷基硼酸酯。
J Am Chem Soc. 2022 Aug 24;144(33):15333-15338. doi: 10.1021/jacs.2c06488. Epub 2022 Aug 11.