• 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

分子间金属催化未活化醇或醛的C-C偶联反应用于构建超越预金属化试剂的收敛性酮类化合物。

Intermolecular Metal-Catalyzed C‒C Coupling of Unactivated Alcohols or Aldehydes for Convergent Ketone Construction beyond Premetalated Reagents.

作者信息

Spinello Brian J, Strong Zachary H, Ortiz Eliezer, Evarts Maddie M, Krische Michael J

机构信息

University of Texas at Austin, Department of Chemistry, Welch Hall (A5300), 105 E 24 St., Austin, TX 78712, USA.

出版信息

ACS Catal. 2023 Aug 18;13(16):10976-10987. doi: 10.1021/acscatal.3c02209. Epub 2023 Aug 4.

DOI:10.1021/acscatal.3c02209
PMID:38464997
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10923551/
Abstract

Intermolecular metal-catalyzed C‒C couplings of unactivated primary alcohols or aldehydes to form ketones are catalogued. Reactions are classified on the basis of pronucleophile. Protocols involving premetalated reagents or reactants that incorporate directing groups are not covered. These methods represent an emerging alternative to classical multi-step protocols for ketone construction that exploit premetalated reagents, and/or steps devoted to redox manipulations and carboxylic acid derivatization.

摘要

未活化的伯醇或醛分子间金属催化的C-C偶联反应生成酮的反应已被编目。反应根据亲核试剂进行分类。涉及预金属化试剂或含有导向基团的反应物的方案不包括在内。这些方法是用于构建酮的经典多步方案的新兴替代方法,经典方案利用预金属化试剂和/或涉及氧化还原操作和羧酸衍生化的步骤。

相似文献

1
Intermolecular Metal-Catalyzed C‒C Coupling of Unactivated Alcohols or Aldehydes for Convergent Ketone Construction beyond Premetalated Reagents.分子间金属催化未活化醇或醛的C-C偶联反应用于构建超越预金属化试剂的收敛性酮类化合物。
ACS Catal. 2023 Aug 18;13(16):10976-10987. doi: 10.1021/acscatal.3c02209. Epub 2023 Aug 4.
2
Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.通过醇介导的氢转移实现的手性催化羰基烯丙基化和炔丙基化:格氏试剂和萨巴蒂埃反应的化学融合。
Acc Chem Res. 2017 Sep 19;50(9):2371-2380. doi: 10.1021/acs.accounts.7b00308. Epub 2017 Aug 9.
3
Transition-Metal-Catalyzed C-C Bond Formation from C-C Activation.过渡金属催化的由碳-碳活化形成碳-碳键
Acc Chem Res. 2023 Nov 7;56(21):2867-2886. doi: 10.1021/acs.accounts.3c00230. Epub 2023 Oct 26.
4
Reductive Cross-Coupling of Unreactive Electrophiles.惰性亲电试剂的还原交叉偶联。
Acc Chem Res. 2022 Sep 6;55(17):2491-2509. doi: 10.1021/acs.accounts.2c00381. Epub 2022 Aug 11.
5
Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.三氟甲磺酸乙烯酯-醛还原偶联-由甲酸盐介导的氧化还原异构化:铑催化酮合成在无化学计量金属的情况下。
Chemistry. 2019 Sep 25;25(54):12517-12520. doi: 10.1002/chem.201903668. Epub 2019 Sep 4.
6
Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.炔烃与羰基化合物及亚胺的对映选择性金属催化还原偶联:烯丙醇和烯丙胺的汇聚式构建
ACS Catal. 2022 Jul 15;12(14):8164-8174. doi: 10.1021/acscatal.2c02444. Epub 2022 Jun 23.
7
Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.通过位点选择性氧化还原引发的羰基加成实现手性二醇的不对称铱催化C-C偶联反应。
Top Curr Chem. 2016;372:85-101. doi: 10.1007/128_2015_651.
8
Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones.通过钌催化的形成碳-碳键的转移氢化反应,从醇或醛氧化水平进行二烯氢酰化反应:β,γ-不饱和酮的合成。
J Am Chem Soc. 2008 Oct 29;130(43):14120-2. doi: 10.1021/ja805356j. Epub 2008 Oct 8.
9
Transition-Metal-Catalyzed Cross-Coupling with Ketones or Aldehydes via -Tosylhydrazones.过渡金属催化的酮或醛与 - 对甲苯磺酰腙的交叉偶联反应。
J Am Chem Soc. 2020 Jun 17;142(24):10592-10605. doi: 10.1021/jacs.0c04445. Epub 2020 Jun 6.
10
Cross-dehydrogenative coupling for the intermolecular C-O bond formation.交叉脱氢偶联反应在分子间 C-O 键形成中的应用。
Beilstein J Org Chem. 2015 Jan 20;11:92-146. doi: 10.3762/bjoc.11.13. eCollection 2015.

引用本文的文献

1
Formate-Mediated C-C Coupling of Aryl/Vinyl Halides and Triflates: Carbonyl Arylation and Reductive Cross-Coupling.甲酸盐介导的芳基/乙烯基卤化物与三氟甲磺酸盐的C-C偶联:羰基芳基化和还原交叉偶联
ACS Catal. 2025 May 16;15(10):8274-8283. doi: 10.1021/acscatal.5c01994. Epub 2025 May 2.
2
Dehomologative C-C Borylation of Aldehydes and Alcohols via a Rh-Catalyzed Dehydroformylation-Borylation Relay.通过铑催化的脱氢甲酰化-硼化接力实现醛和醇的去同系化碳-碳硼化反应
J Am Chem Soc. 2025 May 21;147(20):16735-16741. doi: 10.1021/jacs.5c02181. Epub 2025 May 12.
3
Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis.

本文引用的文献

1
Ruthenium-Catalyzed C-C Coupling of Terminal Alkynes with Primary Alcohols or Aldehydes: α,β-Acetylenic Ketones (Ynones) via Oxidative Alkynylation.钌催化的末端炔烃与伯醇或醛的 C-C 偶联:通过氧化炔基化生成α,β-乙炔基酮(Ynones)。
Angew Chem Int Ed Engl. 2023 Jun 5;62(23):e202303345. doi: 10.1002/anie.202303345. Epub 2023 Apr 26.
2
Progress in C-C and C-Heteroatom Bonds Construction Using Alcohols as Acyl Precursors.醇作为酰基前体构建 C-C 和 C-杂原子键的研究进展。
Molecules. 2022 Dec 16;27(24):8977. doi: 10.3390/molecules27248977.
3
Nickel-catalyzed cross-coupling of epoxides with aryltriflates: rapid and regioselective construction of aryl ketones.
通过双光/钴催化实现由伯醇和烯烃直接合成酮。
Nat Commun. 2024 Aug 9;15(1):6816. doi: 10.1038/s41467-024-51190-3.
镍催化环氧化物与芳基三氟甲磺酸酯的交叉偶联反应:快速和区域选择性构建芳基酮。
Chem Commun (Camb). 2022 Aug 16;58(66):9214-9217. doi: 10.1039/d2cc02891c.
4
Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer.理解卤化物抗衡离子在对映选择性钌催化羰基(α-芳基)烯丙基化反应中的作用:炔烃作为潜伏的烯丙基化合物,以及三氟乙醇在氢自动转移转化乙醇为更高醇中的增强转化。
J Am Chem Soc. 2021 Oct 13;143(40):16709-16717. doi: 10.1021/jacs.1c07857. Epub 2021 Oct 4.
5
Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.通过铑催化的合并转移氢化羰基加成-氧化还原异构化反应将伯醇和丁二烯转化为支链酮
J Am Chem Soc. 2021 Sep 1;143(34):13507-13512. doi: 10.1021/jacs.1c07230. Epub 2021 Aug 20.
6
α- and β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- and Enantioselectivity in Hydroacylation of 1,3-Dienes.α-和β-官能化酮类化合物的合成:1,3-二烯与醛的反应中区域和对映选择性控制。 在 1,3-二烯的氢甲酰化反应中。
J Am Chem Soc. 2021 Aug 18;143(32):12825-12835. doi: 10.1021/jacs.1c06245. Epub 2021 Aug 5.
7
Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.烯丙基试剂和二烯作为手性烯丙基金属亲核试剂在催化对映选择性 C=X 加成反应中的应用:历史透视和最新进展综述。
Chemistry. 2021 Sep 15;27(52):13107-13116. doi: 10.1002/chem.202101890. Epub 2021 Jul 29.
8
Cross-coupling reactions with esters, aldehydes, and alcohols.酯、醛和醇的交叉偶联反应。
Chem Commun (Camb). 2021 Mar 11;57(21):2591-2604. doi: 10.1039/d0cc08389e.
9
Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl -(α-Aryl)allylation.对映选择性和非对映选择性钌催化 1-芳基丙炔与醇的 C-C 偶联反应:炔烃作为手性烯丙基金属前体在羰基-(α-芳基)烯丙基化反应中的应用。
J Am Chem Soc. 2021 Feb 24;143(7):2838-2845. doi: 10.1021/jacs.0c12242. Epub 2021 Feb 8.
10
Mechanism of nickel-catalyzed direct carbonyl-Heck coupling reaction: the crucial role of second-sphere interactions.镍催化的直接羰基-Heck偶联反应机理:二级相互作用的关键作用。
Dalton Trans. 2021 Feb 23;50(7):2654-2662. doi: 10.1039/d0dt04121a.