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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。

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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.

ACS Catal. 2025-5-16

[2]
Dehomologative C-C Borylation of Aldehydes and Alcohols via a Rh-Catalyzed Dehydroformylation-Borylation Relay.

J Am Chem Soc. 2025-5-21

[3]
Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis.

Nat Commun. 2024-8-9

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.

Angew Chem Int Ed Engl. 2023-6-5

[2]
Progress in C-C and C-Heteroatom Bonds Construction Using Alcohols as Acyl Precursors.

Molecules. 2022-12-16

[3]
Nickel-catalyzed cross-coupling of epoxides with aryltriflates: rapid and regioselective construction of aryl ketones.

Chem Commun (Camb). 2022-8-16

[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.

J Am Chem Soc. 2021-10-13

[5]
Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.

J Am Chem Soc. 2021-9-1

[6]
α- and β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- and Enantioselectivity in Hydroacylation of 1,3-Dienes.

J Am Chem Soc. 2021-8-18

[7]
Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Chemistry. 2021-9-15

[8]
Cross-coupling reactions with esters, aldehydes, and alcohols.

Chem Commun (Camb). 2021-3-11

[9]
Diastereo- and Enantioselective Ruthenium-Catalyzed C-C Coupling of 1-Arylpropynes and Alcohols: Alkynes as Chiral Allylmetal Precursors in Carbonyl -(α-Aryl)allylation.

J Am Chem Soc. 2021-2-24

[10]
Mechanism of nickel-catalyzed direct carbonyl-Heck coupling reaction: the crucial role of second-sphere interactions.

Dalton Trans. 2021-2-23

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