• 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

金催化的炔丙位取代反应：范围和合成进展。

Gold-catalyzed propargylic substitutions: Scope and synthetic developments.

机构信息

Institut Charles Gerhardt, UMR 5253, Equipe AM2N, ENSCM 8 rue de l'Ecole Normale, 34296 Montpellier Cédex, France.

出版信息

Beilstein J Org Chem. 2011;7:866-77. doi: 10.3762/bjoc.7.99. Epub 2011 Jun 28.

DOI:10.3762/bjoc.7.99
PMID:21804883
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3135077/
Abstract

This personal account summarizes our recent developments in gold-catalyzed direct substitutions on propargylic (allylic, benzylic) alcohols, with various nucleophiles (and bi-nucleophiles) based on the σ- and/or π-acidity of gold(III) complexes. Synthetic developments are also briefly described.

摘要

这篇个人述评总结了我们最近在金催化炔丙基（烯丙基、苄基）醇的直接取代反应方面的进展，涉及各种亲核试剂（和双亲核试剂），基于金(III)配合物的σ-和/或π-酸性。合成方面的发展也做了简要描述。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/78052579aaff/Beilstein_J_Org_Chem-07-866-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/39290d14c626/Beilstein_J_Org_Chem-07-866-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/2e564bece6f1/Beilstein_J_Org_Chem-07-866-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/036905553a6b/Beilstein_J_Org_Chem-07-866-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/c5df54c19b53/Beilstein_J_Org_Chem-07-866-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7119eeda257a/Beilstein_J_Org_Chem-07-866-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/3821e3efcf98/Beilstein_J_Org_Chem-07-866-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/2a54289b1aa9/Beilstein_J_Org_Chem-07-866-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/f7c93674e39d/Beilstein_J_Org_Chem-07-866-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/b2bd1a75cac3/Beilstein_J_Org_Chem-07-866-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/59449cf1cc8f/Beilstein_J_Org_Chem-07-866-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7f2d7902b8aa/Beilstein_J_Org_Chem-07-866-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7bafec834e66/Beilstein_J_Org_Chem-07-866-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/8b9923435804/Beilstein_J_Org_Chem-07-866-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/e9227d0b5c3a/Beilstein_J_Org_Chem-07-866-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/8f20a8d9c981/Beilstein_J_Org_Chem-07-866-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/a6daaa2daad9/Beilstein_J_Org_Chem-07-866-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/d4206aab0ef6/Beilstein_J_Org_Chem-07-866-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/6e7082b94d2b/Beilstein_J_Org_Chem-07-866-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/f3b7189fe4b5/Beilstein_J_Org_Chem-07-866-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/78052579aaff/Beilstein_J_Org_Chem-07-866-g021.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/39290d14c626/Beilstein_J_Org_Chem-07-866-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/2e564bece6f1/Beilstein_J_Org_Chem-07-866-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/036905553a6b/Beilstein_J_Org_Chem-07-866-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/c5df54c19b53/Beilstein_J_Org_Chem-07-866-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7119eeda257a/Beilstein_J_Org_Chem-07-866-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/3821e3efcf98/Beilstein_J_Org_Chem-07-866-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/2a54289b1aa9/Beilstein_J_Org_Chem-07-866-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/f7c93674e39d/Beilstein_J_Org_Chem-07-866-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/b2bd1a75cac3/Beilstein_J_Org_Chem-07-866-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/59449cf1cc8f/Beilstein_J_Org_Chem-07-866-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7f2d7902b8aa/Beilstein_J_Org_Chem-07-866-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/7bafec834e66/Beilstein_J_Org_Chem-07-866-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/8b9923435804/Beilstein_J_Org_Chem-07-866-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/e9227d0b5c3a/Beilstein_J_Org_Chem-07-866-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/8f20a8d9c981/Beilstein_J_Org_Chem-07-866-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/a6daaa2daad9/Beilstein_J_Org_Chem-07-866-g017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/d4206aab0ef6/Beilstein_J_Org_Chem-07-866-g018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/6e7082b94d2b/Beilstein_J_Org_Chem-07-866-g019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/f3b7189fe4b5/Beilstein_J_Org_Chem-07-866-g020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0ced/3135077/78052579aaff/Beilstein_J_Org_Chem-07-866-g021.jpg

相似文献

1
Gold-catalyzed propargylic substitutions: Scope and synthetic developments.金催化的炔丙位取代反应：范围和合成进展。
Beilstein J Org Chem. 2011;7:866-77. doi: 10.3762/bjoc.7.99. Epub 2011 Jun 28.
2
A versatile iron-catalyzed protocol for the one-pot synthesis of isoxazoles or isoxazolines from the same propargylic alcohols.一种多功能的铁催化一锅法，可从同一丙炔醇合成异恶唑或异恶唑啉。
Chemistry. 2010 Oct 25;16(40):12207-13. doi: 10.1002/chem.201001461.
3
Facile coupling of propargylic, allylic and benzylic alcohols with allylsilane and alkynylsilane, and their deoxygenation with Et3SiH, catalyzed by Bi(OTf)3 in [BMIM][BF4] ionic liquid (IL), with recycling and reuse of the IL.三氟甲磺酸铋（Bi(OTf)3）在 [BMIM][BF4] 离子液体（IL）中催化炔基硅烷和烯丙基硅烷与丙炔基、烯丙基和苄基醇的简便偶联反应，以及它们的脱氧反应，离子液体可回收和重复使用。
Org Biomol Chem. 2012 Sep 28;10(36):7347-55. doi: 10.1039/c2ob26046h.
4
Ruthenium-catalyzed propargylic substitution reactions of propargylic alcohols with oxygen-, nitrogen-, and phosphorus-centered nucleophiles.钌催化的炔丙醇与以氧、氮和磷为中心的亲核试剂的炔丙基取代反应。
Chemistry. 2005 Feb 18;11(5):1433-51. doi: 10.1002/chem.200400833.
5
Gold(III)-catalyzed nucleophilic substitution of propargylic alcohols.金（III）催化的炔丙醇亲核取代反应。
J Am Chem Soc. 2005 Oct 19;127(41):14180-1. doi: 10.1021/ja0534147.
6
Gold-catalyzed cyclization reactions of allenol and alkynol derivatives.金催化的烯丙醇和炔丙醇衍生物的环化反应。
Acc Chem Res. 2014 Mar 18;47(3):939-52. doi: 10.1021/ar4002558. Epub 2014 Jan 15.
7
Ruthenium-catalyzed propargylic substitution reaction of propargylic alcohols with thiols: a general synthetic route to propargylic sulfides.钌催化炔丙醇与硫醇的炔丙基取代反应：合成炔丙基硫醚的通用路线。
J Am Chem Soc. 2002 Dec 25;124(51):15172-3. doi: 10.1021/ja027754t.
8
Palladium-catalyzed cyclization of propargylic compounds.钯催化炔丙基化合物的环化反应。
Acc Chem Res. 2011 Feb 15;44(2):111-22. doi: 10.1021/ar100109m. Epub 2010 Oct 28.
9
Ruthenium-Catalyzed Enantioselective Propargylic Phosphinylation of Propargylic Alcohols with Phosphine Oxides.钌催化炔丙醇与氧化膦的对映选择性炔丙基膦酰化反应
Angew Chem Int Ed Engl. 2021 May 10;60(20):11231-11236. doi: 10.1002/anie.202102779. Epub 2021 Apr 7.
10
Gold self-relay catalysis enabling annulative oxygenation of propargylic alcohols with O-nucleophiles.金自接力催化实现炔丙醇与氧亲核试剂的环化氧化反应。
Chem Commun (Camb). 2023 Mar 30;59(27):4032-4035. doi: 10.1039/d3cc00089c.

引用本文的文献

1
An Organometallic Umpolung Approach for Iron-Mediated Propargylic C-H Etherification.一种用于铁介导的炔丙基C-H醚化反应的有机金属极性反转方法。
Angew Chem Int Ed Engl. 2024 Dec 20;63(52):e202413017. doi: 10.1002/anie.202413017. Epub 2024 Nov 20.
2
Scope and advances in the catalytic propargylic substitution reaction.催化炔丙基取代反应的范围与进展
RSC Adv. 2018 Sep 5;8(54):31129-31193. doi: 10.1039/c8ra04481c. eCollection 2018 Aug 30.
3
Tunable Gold-catalyzed Reactions of Propargyl Alcohols and Aryl Nucleophiles.可调节的金催化炔丙醇与芳基亲核试剂反应。

本文引用的文献

1
Gold-catalyzed carbon-heteroatom bond-forming reactions.金催化的碳-杂原子成键反应。
Chem Rev. 2011 Mar 9;111(3):1657-712. doi: 10.1021/cr100414u.
2
A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature.一种在室温下通过金催化炔丙醇的 Meyer-Schuster 重排反应合成烯酮的通用方法。
J Org Chem. 2011 Mar 4;76(5):1479-82. doi: 10.1021/jo102263t. Epub 2011 Jan 25.
3
Gold-catalyzed direct activation of allylic alcohols in the stereoselective synthesis of functionalized 2-vinyl-morpholines.
ChemistryOpen. 2022 May;11(5):e202200030. doi: 10.1002/open.202200030. Epub 2022 Mar 10.
金催化烯丙醇在功能化2-乙烯基吗啉立体选择性合成中的直接活化作用。
Chemistry. 2010 Dec 27;16(48):14272-7. doi: 10.1002/chem.201002606.
4
A versatile iron-catalyzed protocol for the one-pot synthesis of isoxazoles or isoxazolines from the same propargylic alcohols.一种多功能的铁催化一锅法，可从同一丙炔醇合成异恶唑或异恶唑啉。
Chemistry. 2010 Oct 25;16(40):12207-13. doi: 10.1002/chem.201001461.
5
Highly diastereoselective Baldwin rearrangement of isoxazolines into cis-acylaziridines.高度非对映选择性异恶唑啉的Baldwin 重排反应生成顺式酰基氮丙啶。
J Org Chem. 2010 Sep 3;75(17):6050-3. doi: 10.1021/jo101273d.
6
Direct synthesis of trisubstituted isoxazoles through gold-catalyzed domino reaction of alkynyl oxime ethers.通过金催化的炔基肟醚的多步反应直接合成三取代异恶唑。
Org Lett. 2010 Jun 4;12(11):2594-7. doi: 10.1021/ol100803e.
7
Remarkable anion effects uncovered in the development of a Au(III)-catalyzed tandem nucleophilic substitution-1,5-enyne cycloisomerization process.在 Au(III)催化的串联亲核取代-1,5-炔环异构化反应过程中发现显著的阴离子效应。
Chem Commun (Camb). 2010 Mar 28;46(12):2046-8. doi: 10.1039/b925919h. Epub 2010 Feb 15.
8
Stereoselective reactions with stabilized carbocations.与稳定碳正离子的立体选择性反应。
Angew Chem Int Ed Engl. 2010;49(2):256-9. doi: 10.1002/anie.200905235.
9
An efficient synthesis of (+/-)-grandisol featuring 1,5-enyne metathesis.（+/-）-grandisol 的高效合成，其特征在于 1,5-烯炔复分解。
J Org Chem. 2010 Jan 1;75(1):226-8. doi: 10.1021/jo9020375.
10
Enantioselective gold-catalyzed allylic alkylation of indoles with alcohols: an efficient route to functionalized tetrahydrocarbazoles.铟与醇的对映选择性金催化烯丙基烷基化反应：一种合成官能化四氢咔唑的有效途径。
Angew Chem Int Ed Engl. 2009;48(50):9533-7. doi: 10.1002/anie.200904388.