• 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

α-酰胺醛作为铑催化分子间炔烃氢酰化反应的底物：α-酰胺酮的合成

α-Amidoaldehydes as Substrates in Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α-Amidoketones.

作者信息

Pal Ritashree, O'Brien Sean C, Willis Michael C

机构信息

Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom.

出版信息

Chemistry. 2020 Sep 10;26(51):11710-11714. doi: 10.1002/chem.202002478. Epub 2020 Jul 30.

DOI:10.1002/chem.202002478
PMID:32449532
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7540332/
Abstract

We show that readily available α-amidoaldehydes are effective substrates for intermolecular Rh-catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C H F)][BAr ] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α-amidoketone products. High yields and high levels of regioselectivity are achieved. The use of α-amidoaldehydes as substrates establishes that 1,4-dicarbonyl motifs can be used as controlling groups in Rh-catalyzed hydroacylation reactions.

摘要

我们表明，易于获得的α-酰胺醛是分子间铑催化的炔烃氢酰化反应的有效底物。催化剂[Rh(dppe)(CHF)][BAr]具有良好的反应活性，能使多种醛和炔烃用作底物，生成α-酰胺基酮产物。实现了高产率和高区域选择性。使用α-酰胺醛作为底物表明，1,4-二羰基基序可作为铑催化氢酰化反应中的控制基团。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/b0ac467f0a16/CHEM-26-11710-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/b65ada99aec9/CHEM-26-11710-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/55b0fc69fd1a/CHEM-26-11710-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/71078daef7d0/CHEM-26-11710-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/ed972696f4e0/CHEM-26-11710-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/b0ac467f0a16/CHEM-26-11710-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/b65ada99aec9/CHEM-26-11710-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/55b0fc69fd1a/CHEM-26-11710-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/71078daef7d0/CHEM-26-11710-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/ed972696f4e0/CHEM-26-11710-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cd58/7540332/b0ac467f0a16/CHEM-26-11710-g005.jpg

相似文献

1
α-Amidoaldehydes as Substrates in Rhodium-Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α-Amidoketones.α-酰胺醛作为铑催化分子间炔烃氢酰化反应的底物：α-酰胺酮的合成
Chemistry. 2020 Sep 10;26(51):11710-11714. doi: 10.1002/chem.202002478. Epub 2020 Jul 30.
2
Exploiting Carbonyl Groups to Control Intermolecular Rhodium-Catalyzed Alkene and Alkyne Hydroacylation.利用羰基基团控制铑催化的烯烃和炔烃氢甲酰化反应的分子间反应。
J Am Chem Soc. 2017 Jul 26;139(29):10142-10149. doi: 10.1021/jacs.7b05713. Epub 2017 Jul 17.
3
Rhodium-catalyzed intermolecular chelation controlled alkene and alkyne hydroacylation: synthetic scope of beta-S-substituted aldehyde substrates.铑催化的分子间螯合控制的烯烃和炔烃氢酰化反应：β-S-取代醛底物的合成范围
J Org Chem. 2006 Jul 7;71(14):5291-7. doi: 10.1021/jo060582o.
4
Azine-N-oxides as effective controlling groups for Rh-catalysed intermolecular alkyne hydroacylation.吖嗪氮氧化物作为铑催化分子间炔烃氢酰化反应的有效控制基团。
Chem Sci. 2021 Sep 14;12(39):13068-13073. doi: 10.1039/d1sc03915f. eCollection 2021 Oct 13.
5
O-substituted alkyl aldehydes for rhodium-catalyzed intermolecular alkyne hydroacylation: the utility of methylthiomethyl ethers.铑催化的炔烃分子间氢甲酰化反应中 O-取代的烷基醛：甲硫甲基醚的用途。
Org Lett. 2011 Mar 4;13(5):998-1000. doi: 10.1021/ol1030662. Epub 2011 Feb 10.
6
Chelation-controlled intermolecular alkene and alkyne hydroacylation: the utility of beta-thioacetal aldehydes.螯合控制的分子间烯烃和炔烃氢酰化反应：β-硫代缩醛醛的效用
Org Lett. 2005 May 26;7(11):2249-51. doi: 10.1021/ol050638l.
7
Intermolecular alkene and alkyne hydroacylation with beta-S-substituted aldehydes: mechanistic insight into the role of a hemilabile P-O-P ligand.分子间烯烃和炔烃与β-S-取代醛的氢酰化反应：对半不稳定P-O-P配体作用的机理洞察
Chemistry. 2008;14(27):8383-97. doi: 10.1002/chem.200800738.
8
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.串联炔烃氢酰化反应与氧杂-Michael加成反应：2,3-二取代苯并二氢吡喃-4-酮及其氟化衍生物的非对映选择性合成
Org Lett. 2015 Jul 2;17(13):3276-9. doi: 10.1021/acs.orglett.5b01447. Epub 2015 Jun 22.
9
α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation.α-氨基酸醛作为易得的手性醛在 Rh 催化炔烃氢甲酰化反应中的应用。
J Am Chem Soc. 2016 Feb 10;138(5):1630-4. doi: 10.1021/jacs.5b11892. Epub 2016 Jan 28.
10
Traceless chelation-controlled rhodium-catalyzed intermolecular alkene and alkyne hydroacylation.无痕迹螯合控制铑催化的烯烃和炔烃的分子间氢甲酰化反应。
Chemistry. 2013 Feb 25;19(9):3125-30. doi: 10.1002/chem.201204056. Epub 2013 Jan 16.

引用本文的文献

1
Diverse saturated heterocycles from a hydroacylation/conjugate addition cascade.通过氢酰化/共轭加成串联反应得到的多种饱和杂环化合物。
Chem Sci. 2022 Jan 19;13(5):1504-1511. doi: 10.1039/d1sc06900d. eCollection 2022 Feb 2.

本文引用的文献

1
A comprehensive review on biological activities of oxazole derivatives.恶唑衍生物生物活性的综合综述。
BMC Chem. 2019 Feb 4;13(1):16. doi: 10.1186/s13065-019-0531-9. eCollection 2019 Dec.
2
Rh(DPEPhos)-Catalyzed Alkyne Hydroacylation Using β-Carbonyl-Substituted Aldehydes: Mechanistic Insight Leads to Low Catalyst Loadings that Enables Selective Catalysis on Gram-Scale.Rh(DPEPhos)-催化的炔烃氢酰化反应：β-羰基取代醛的应用：机理研究揭示了低催化剂负载量的可能性，从而实现了克级规模的选择性催化。
J Am Chem Soc. 2018 Jun 13;140(23):7347-7357. doi: 10.1021/jacs.8b04086. Epub 2018 May 29.
3
Recent advance in oxazole-based medicinal chemistry.
基于恶唑的药物化学的最新进展。
Eur J Med Chem. 2018 Jan 20;144:444-492. doi: 10.1016/j.ejmech.2017.12.044. Epub 2017 Dec 14.
4
Exploiting Carbonyl Groups to Control Intermolecular Rhodium-Catalyzed Alkene and Alkyne Hydroacylation.利用羰基基团控制铑催化的烯烃和炔烃氢甲酰化反应的分子间反应。
J Am Chem Soc. 2017 Jul 26;139(29):10142-10149. doi: 10.1021/jacs.7b05713. Epub 2017 Jul 17.
5
Sequential catalysis: exploiting a single rhodium(i) catalyst to promote an alkyne hydroacylation-aryl boronic acid conjugate addition sequence.连续催化：利用单一铑（I）催化剂促进炔烃氢酰化-芳基硼酸共轭加成序列反应
Chem Sci. 2017 Jan 1;8(1):536-540. doi: 10.1039/c6sc03066a. Epub 2016 Sep 9.
6
Synthesis of α-Amidoketones from Vinyl Esters via a Catalytic/Thermal Cascade Reaction.通过催化/热级联反应从乙烯基酯合成α-酰胺酮。
J Org Chem. 2016 Jun 3;81(11):4823-8. doi: 10.1021/acs.joc.5b02851. Epub 2016 May 19.
7
Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones.1,2-叠氮醇酯催化转化为α-酰胺基酮。
Chem Commun (Camb). 2016 May 5;52(39):6549-52. doi: 10.1039/c6cc02063a.
8
α-Amino Aldehydes as Readily Available Chiral Aldehydes for Rh-Catalyzed Alkyne Hydroacylation.α-氨基酸醛作为易得的手性醛在 Rh 催化炔烃氢甲酰化反应中的应用。
J Am Chem Soc. 2016 Feb 10;138(5):1630-4. doi: 10.1021/jacs.5b11892. Epub 2016 Jan 28.
9
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.串联炔烃氢酰化反应与氧杂-Michael加成反应：2,3-二取代苯并二氢吡喃-4-酮及其氟化衍生物的非对映选择性合成
Org Lett. 2015 Jul 2;17(13):3276-9. doi: 10.1021/acs.orglett.5b01447. Epub 2015 Jun 22.
10
2-Aminobenzaldehydes as versatile substrates for rhodium-catalyzed alkyne hydroacylation: application to dihydroquinolone synthesis.2-氨基苯甲醛作为铑催化炔烃氢酰化反应的通用底物：在二氢喹诺酮合成中的应用
Angew Chem Int Ed Engl. 2013 Dec 9;52(50):13280-3. doi: 10.1002/anie.201308127. Epub 2013 Nov 12.