使用乙腈，通过1,4 - 双（三甲基硅基）- 2,3,5,6 - 四甲基 - 1,4 - 二氢吡嗪辅助的C - CN键裂解，实现镍催化的芳基卤化物和三氟甲磺酸酯的氰化反应。

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine.

作者信息

Ueda Yohei, Tsujimoto Nagataka, Yurino Taiga, Tsurugi Hayato, Mashima Kazushi

机构信息

Department of Chemistry , Graduate School of Engineering Science , Osaka University , Toyonaka , Osaka 560-8531 , Japan . Email:

出版信息

Chem Sci. 2018 Nov 26;10(4):994-999. doi: 10.1039/c8sc04437f. eCollection 2019 Jan 28.

DOI:10.1039/c8sc04437f

PMID:30774893

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6349056/

Abstract

We developed a non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of Ni(MeCN), 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (-Me-DHP). -Me-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation C-CN bond cleavage.

摘要

我们利用Ni(MeCN)、1,10-菲咯啉和1,4-双(三甲基硅基)-2,3,5,6-四甲基-1,4-二氢吡嗪(-Me-DHP)的催化剂体系，在乙腈中开发了各种芳基卤化物和三氟甲磺酸酯的无毒氰化反应。发现-Me-DHP作为一种还原剂用于生成零价镍物种，以及作为一种硅烷化试剂以实现催化氰化C-CN键的裂解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f7ba/6349056/d9dcba1f53f8/c8sc04437f-f1.jpg

相似文献

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine.

Chem Sci. 2018 Nov 26;10(4):994-999. doi: 10.1039/c8sc04437f. eCollection 2019 Jan 28.

Salt-Free Reduction of Transition Metal Complexes by Bis(trimethylsilyl)cyclohexadiene, -dihydropyrazine, and -4,4'-bipyridinylidene Derivatives.

Acc Chem Res. 2019 Mar 19;52(3):769-779. doi: 10.1021/acs.accounts.8b00638. Epub 2019 Feb 22.

Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling.

Angew Chem Int Ed Engl. 2017 Dec 4;56(49):15693-15697. doi: 10.1002/anie.201707517. Epub 2017 Nov 7.

Light-Triggered, Ni-Catalyzed Cyanation of Aryl Triflates with 1,4-Dicyanobenzene as the CN Source.

Org Lett. 2024 Feb 23;26(7):1370-1375. doi: 10.1021/acs.orglett.3c04294. Epub 2024 Feb 15.

Nickel-Catalyzed Cyanation of (Hetero)aryl Bromides Using DABAL-Me as a Soluble Reductant.

Org Lett. 2022 Nov 18;24(45):8397-8400. doi: 10.1021/acs.orglett.2c03503. Epub 2022 Nov 9.

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Org Lett. 2015 Jan 16;17(2):202-5. doi: 10.1021/ol5032359. Epub 2015 Jan 2.

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation.

J Am Chem Soc. 2019 Dec 11;141(49):19257-19262. doi: 10.1021/jacs.9b11208. Epub 2019 Nov 25.

Photochemically Enabled, Ni-Catalyzed Cyanation of Aryl Halides.

Org Lett. 2022 Apr 1;24(12):2271-2275. doi: 10.1021/acs.orglett.2c00203. Epub 2022 Mar 22.

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN): Key Roles of DMAP.

Org Lett. 2017 Apr 21;19(8):2118-2121. doi: 10.1021/acs.orglett.7b00732. Epub 2017 Apr 5.

Cross-Couplings Using Aryl Ethers via C-O Bond Activation Enabled by Nickel Catalysts.

Acc Chem Res. 2015 Jun 16;48(6):1717-26. doi: 10.1021/acs.accounts.5b00051. Epub 2015 Jun 3.

引用本文的文献

Nickel-Catalyzed Cyanation of Aryl Halides.

Molecules. 2025 Aug 20;30(16):3440. doi: 10.3390/molecules30163440.

Ni-Catalyzed Cyanation of (Hetero)Aryl Electrophiles Using the Nontoxic Cyanating Reagent K[Fe(CN)].

ACS Catal. 2025 Apr 5;15(8):6459-6465. doi: 10.1021/acscatal.5c00158. eCollection 2025 Apr 18.

Nickel-Catalyzed Reductive Cyanation of Aryl Halides and Epoxides with Cyanogen Bromide.

Molecules. 2024 Dec 20;29(24):6016. doi: 10.3390/molecules29246016.

ZnCoO@g-CN@Cu as a new and highly efficient heterogeneous photocatalyst for visible light-induced cyanation and Mizoroki-Heck cross-coupling reactions.

RSC Adv. 2024 Aug 22;14(36):26424-26436. doi: 10.1039/d4ra04827j. eCollection 2024 Aug 16.

Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

J Org Chem. 2022 Jun 17;87(12):7589-7609. doi: 10.1021/acs.joc.2c00462. Epub 2022 Jun 7.

Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

J Am Chem Soc. 2021 Dec 15;143(49):21024-21036. doi: 10.1021/jacs.1c10932. Epub 2021 Nov 30.

Extensive Redox Non-Innocence in Iron Bipyridine-Diimine Complexes: a Combined Spectroscopic and Computational Study.

Inorg Chem. 2021 Dec 6;60(23):18296-18306. doi: 10.1021/acs.inorgchem.1c02925. Epub 2021 Nov 17.

Chromium-catalyzed cyclopropanation of alkenes with bromoform in the presence of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine.

Chem Sci. 2020 Mar 11;11(14):3604-3609. doi: 10.1039/d0sc00964d.

An advancement in the synthesis of nano Pd@magnetic amine-Functionalized UiO-66-NH catalyst for cyanation and O-arylation reactions.

Sci Rep. 2021 May 31;11(1):11387. doi: 10.1038/s41598-021-90478-y.

Reductive cyanation of organic chlorides using CO and NH via Triphos-Ni(I) species.

Nat Commun. 2020 Aug 14;11(1):4096. doi: 10.1038/s41467-020-17939-2.

本文引用的文献

Nickel-Catalyzed Copolymerization of Ethylene and Vinyltrialkoxysilanes: Catalytic Production of Cross-Linkable Polyethylene and Elucidation of the Chain-Growth Mechanism.

J Am Chem Soc. 2017 Nov 8;139(44):16013-16022. doi: 10.1021/jacs.7b10281. Epub 2017 Oct 30.

Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling.

Angew Chem Int Ed Engl. 2017 Dec 4;56(49):15693-15697. doi: 10.1002/anie.201707517. Epub 2017 Nov 7.

Nickel-Catalyzed C-H Silylation of Arenes with Vinylsilanes: Rapid and Reversible β-Si Elimination.

J Am Chem Soc. 2017 Jul 12;139(27):9401-9407. doi: 10.1021/jacs.7b05574. Epub 2017 Jun 23.

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN): Key Roles of DMAP.

Org Lett. 2017 Apr 21;19(8):2118-2121. doi: 10.1021/acs.orglett.7b00732. Epub 2017 Apr 5.

Cyanation of Phenol Derivatives with Aminoacetonitriles by Nickel Catalysis.

Org Lett. 2016 Sep 2;18(17):4428-31. doi: 10.1021/acs.orglett.6b02265. Epub 2016 Aug 12.

Salt-Free Reduction of Nonprecious Transition-Metal Compounds: Generation of Amorphous Ni Nanoparticles for Catalytic C-C Bond Formation.

Angew Chem Int Ed Engl. 2015 Nov 23;54(48):14437-41. doi: 10.1002/anie.201507902. Epub 2015 Sep 30.

Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C-CN bond activation.

Org Biomol Chem. 2015 Oct 21;13(39):9963-8. doi: 10.1039/c5ob01675d.

Cu-Catalyzed Cyanation of Indoles with Acetonitrile as a Cyano Source.

J Org Chem. 2015 Sep 4;80(17):8868-73. doi: 10.1021/acs.joc.5b01419. Epub 2015 Aug 26.

Acetonitrile as a cyanating reagent: Cu-catalyzed cyanation of arenes.

Org Lett. 2015 Jun 5;17(11):2602-5. doi: 10.1021/acs.orglett.5b00886. Epub 2015 May 19.

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Org Lett. 2015 Jan 16;17(2):202-5. doi: 10.1021/ol5032359. Epub 2015 Jan 2.

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

使用乙腈，通过1,4 - 双（三甲基硅基）- 2,3,5,6 - 四甲基 - 1,4 - 二氢吡嗪辅助的C - CN键裂解，实现镍催化的芳基卤化物和三氟甲磺酸酯的氰化反应。

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine.

作者信息

机构信息

出版信息

相似文献

引用本文的文献

本文引用的文献

文献AI研究员

用中文搜PubMed

文档翻译

Suppr 超能文献

使用乙腈，通过1,4 - 双（三甲基硅基）- 2,3,5,6 - 四甲基 - 1,4 - 二氢吡嗪辅助的C - CN键裂解，实现镍催化的芳基卤化物和三氟甲磺酸酯的氰化反应。

Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine.

作者信息

机构信息

出版信息

相似文献

引用本文的文献

本文引用的文献