Suppr超能文献

使用第10族金属将简单烯烃催化加成到羰基化合物上。

Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.

作者信息

Ho Chun-Yu, Schleicher Kristin D, Jamison Timothy F

机构信息

Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong SAR (P.R. China).

出版信息

Synlett. 2009 Oct 1;2009(16):2565-2582. doi: 10.1055/s-0029-1217747.

Abstract

Recent advances using nickel complexes in the activation of unactivated monosubstituted olefins for catalytic intermolecular carbon-carbon bond-forming reactions with carbonyl compounds, such as simple aldehydes, isocyanates, and conjugated aldehydes and ketones, are discussed. In these reactions, the olefins function as vinyl- and allylmetal equivalents, providing a new strategy for organic synthesis. Current limitations and the outlook for this new strategy are also discussed.

摘要

本文讨论了利用镍配合物活化未活化的单取代烯烃,以与羰基化合物(如简单醛、异氰酸酯以及共轭醛和酮)进行催化分子间碳-碳键形成反应的最新进展。在这些反应中,烯烃起到乙烯基金属和烯丙基金属等价物的作用,为有机合成提供了一种新策略。本文还讨论了这一新策略目前的局限性和前景。

相似文献

1
Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.
Synlett. 2009 Oct 1;2009(16):2565-2582. doi: 10.1055/s-0029-1217747.
2
CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.
Acc Chem Res. 2020 Jun 16;53(6):1229-1243. doi: 10.1021/acs.accounts.0c00164. Epub 2020 May 13.
4
Nickel-Catalyzed Coupling Reactions of Alkenes.
Pure Appl Chem. 2008;80(5):929-939. doi: 10.1351/pac200880050929.
7
Manganese Alkyl Carbonyl Complexes: From Iconic Stoichiometric Textbook Reactions to Catalytic Applications.
Acc Chem Res. 2022 Sep 20;55(18):2740-2751. doi: 10.1021/acs.accounts.2c00470. Epub 2022 Sep 8.
8
Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery.
Acc Chem Res. 2008 Feb;41(2):222-34. doi: 10.1021/ar700133y. Epub 2008 Feb 2.
9
Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.
Acc Chem Res. 2019 Apr 16;52(4):1134-1144. doi: 10.1021/acs.accounts.9b00044. Epub 2019 Mar 25.

引用本文的文献

1
Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.
ACS Catal. 2022 Feb 18;12(4):2463-2471. doi: 10.1021/acscatal.1c05801. Epub 2022 Feb 3.
2
The Catalytic Asymmetric Intermolecular Prins Reaction.
J Am Chem Soc. 2021 Dec 15;143(49):20598-20604. doi: 10.1021/jacs.1c10245. Epub 2021 Nov 30.
3
Brønsted-Acid-Catalyzed Intramolecular Carbonyl-Olefin Reactions: Interrupted Metathesis vs Carbonyl-Ene Reaction.
J Org Chem. 2021 Feb 5;86(3):3008-3016. doi: 10.1021/acs.joc.0c03021. Epub 2021 Jan 21.
4
Interrupted carbonyl-olefin metathesis via oxygen atom transfer.
Science. 2018 Sep 28;361(6409):1363-1369. doi: 10.1126/science.aar8238.
5
Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers.
Org Lett. 2017 Jan 20;19(2):340-343. doi: 10.1021/acs.orglett.6b03509. Epub 2017 Jan 5.
6
Osmium(0)-Catalyzed C-C Coupling of Ethylene and α-Olefins with Diols, Ketols, or Hydroxy Esters via Transfer Hydrogenation.
J Org Chem. 2016 Sep 16;81(18):8585-94. doi: 10.1021/acs.joc.6b01923. Epub 2016 Sep 8.
7
Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.
J Am Chem Soc. 2016 May 11;138(18):5821-4. doi: 10.1021/jacs.6b03086. Epub 2016 Apr 29.
8
Nickel Catalysis: Synergy between Method Development and Total Synthesis.
Acc Chem Res. 2015 May 19;48(5):1503-14. doi: 10.1021/acs.accounts.5b00064. Epub 2015 Apr 23.
9
A practical and catalytic reductive olefin coupling.
J Am Chem Soc. 2014 Jan 29;136(4):1304-7. doi: 10.1021/ja4117632. Epub 2014 Jan 15.
10
Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.
Top Organomet Chem. 2011 Jan 1;34(2011):107-138. doi: 10.1007/978-3-642-15334-1_5.

本文引用的文献

1
An Efficient Nickel-Catalyzed Cross-Coupling Between sp Carbon Centers.
Angew Chem Int Ed Engl. 1998 Sep 18;37(17):2387-2390. doi: 10.1002/(SICI)1521-3773(19980918)37:17<2387::AID-ANIE2387>3.0.CO;2-M.
2
Nickel-Catalyzed Coupling Reactions of Alkenes.
Pure Appl Chem. 2008;80(5):929-939. doi: 10.1351/pac200880050929.
3
N-heterocyclic carbenes: a new concept in organometallic catalysis.
Angew Chem Int Ed Engl. 2002 Apr 15;41(8):1290-309. doi: 10.1002/1521-3773(20020415)41:8<1290::aid-anie1290>3.0.co;2-y.
4
Highly enantioselective carbonyl-ene reactions catalyzed by In(III)-PyBox complex.
J Am Chem Soc. 2008 Dec 10;130(49):16492-3. doi: 10.1021/ja807501a.
5
Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.
J Am Chem Soc. 2008 Dec 3;130(48):16295-309. doi: 10.1021/ja804659n.
8
Nickel-catalyzed reductive carboxylation of styrenes using CO2.
J Am Chem Soc. 2008 Nov 12;130(45):14936-7. doi: 10.1021/ja8062925. Epub 2008 Oct 17.
10
Synergistic effect of binary component ligands in chiral catalyst library engineering for enantioselective reactions.
Chem Commun (Camb). 2008 Feb 28(8):909-21. doi: 10.1039/b710668h. Epub 2008 Jan 21.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验