Suppr超能文献

通过二叔丁基过氧化物促进的环烷烃C(sp3)[键]H键硫醇化反应无金属制备环烷基芳基硫醚

Metal-Free Preparation of Cycloalkyl Aryl Sulfides via Di-tert-butyl Peroxide-Promoted Oxidative C(sp3)[BOND]H Bond Thiolation of Cycloalkanes.

作者信息

Zhao Jincan, Fang Hong, Han Jianlin, Pan Yi, Li Guigen

机构信息

School of Chemistry and Chemical Engineering, State of Key laboratory of Coordination, Nanjing University, Nanjing, 210093, China.

School of Chemistry and Chemical Engineering, State of Key laboratory of Coordination, Nanjing University, Nanjing, 210093, China ; Institute for Chemistry & BioMedical Sciences, Nanjing University.

出版信息

Adv Synth Catal. 2014 Aug 10;356(11-12):2719-2724. doi: 10.1002/adsc.201400032.

Abstract

A concise thiolation of C(sp)-H bond of cycloalkanes with diaryl disulfides in the presence of oxidant of di--butylperoxide (DTBP) has been developed. This reaction without using any of metal catalyst, tolerates varieties of disulfides and cycloalkanes substrates, giving good to excellent chemical yields, which provides a useful approach to cycloalkyl aryl sulfides from unactivated cycloalkanes.

摘要

已开发出一种在二叔丁基过氧化物(DTBP)氧化剂存在下,环烷烃的C(sp)-H键与二芳基二硫化物的简洁硫醇化反应。该反应不使用任何金属催化剂,能耐受多种二硫化物和环烷烃底物,化学产率良好至优异,为从未活化的环烷烃制备环烷基芳基硫醚提供了一种有用的方法。

相似文献

2
Metal-free oxidative C(sp3)-H bond thiolation of ethers with disulfides.
Org Lett. 2013 Sep 20;15(18):4654-7. doi: 10.1021/ol402281f. Epub 2013 Aug 30.
3
Metal-free oxidative C(sp3)-H bond functionalization of alkanes and conjugate addition to chromones.
Org Lett. 2014 Oct 17;16(20):5342-5. doi: 10.1021/ol502524d. Epub 2014 Sep 25.
6
Palladium-catalyzed thiolation of alkanes and ethers with arylsulfonyl hydrazides.
Chem Commun (Camb). 2014 Aug 11;50(62):8578-81. doi: 10.1039/c4cc02876g.
7
Nickel-catalyzed thiolation of unactivated aryl C-H bonds: efficient access to diverse aryl sulfides.
Chem Commun (Camb). 2015 Mar 7;51(19):4069-72. doi: 10.1039/c4cc10446c.
8
Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process.
Beilstein J Org Chem. 2013 Aug 21;9:1718-23. doi: 10.3762/bjoc.9.197. eCollection 2013.
9
Synthesis of Trisubstituted Vinyl Sulfides via Oxidative Thiolation Initiated Cascade Reaction of Alkynoates with Thiols.
J Org Chem. 2016 Oct 7;81(19):9470-9475. doi: 10.1021/acs.joc.6b01770. Epub 2016 Sep 19.
10
Oxidant controlled regioselective mono- and di-functionalization reactions of coumarins.
Chem Commun (Camb). 2015 Oct 28;51(84):15422-5. doi: 10.1039/c5cc06200d.

引用本文的文献

1
Light-activated hypervalent iodine agents enable diverse aliphatic C-H functionalization.
Nat Chem. 2025 Mar;17(3):365-372. doi: 10.1038/s41557-025-01749-4. Epub 2025 Feb 24.
2
C(sp)-H (N-Phenyltetrazole)thiolation as an Enabling Tool for Molecular Diversification.
Angew Chem Int Ed Engl. 2024 Jul 15;63(29):e202404879. doi: 10.1002/anie.202404879. Epub 2024 Jun 17.
3
Pushing Boundaries: What's Next in Metal-Free C-H Functionalization for Sulfenylation?
Top Curr Chem (Cham). 2024 Apr 12;382(2):13. doi: 10.1007/s41061-024-00460-1.
4
Radical approaches to C-S bonds.
Nat Rev Chem. 2023 Aug;7(8):573-589. doi: 10.1038/s41570-023-00505-x. Epub 2023 Jun 21.
5
Visible-Light-Driven C-S Bond Formation Based on Electron Donor-Acceptor Excitation and Hydrogen Atom Transfer Combined System.
ACS Org Inorg Au. 2021 Jun 22;1(1):23-28. doi: 10.1021/acsorginorgau.1c00007. eCollection 2021 Oct 6.
6
Dealkenylative Thiylation of C(sp)-C(sp) Bonds.
Org Lett. 2019 Nov 1;21(21):8592-8597. doi: 10.1021/acs.orglett.9b03186. Epub 2019 Oct 1.
7
C-H Xanthylation: A Synthetic Platform for Alkane Functionalization.
J Am Chem Soc. 2016 Oct 26;138(42):13854-13857. doi: 10.1021/jacs.6b09414. Epub 2016 Oct 14.
8
Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones.
Monatsh Chem. 2016;147(10):1747-1757. doi: 10.1007/s00706-016-1812-9. Epub 2016 Aug 26.
9
Rearrangements of organic peroxides and related processes.
Beilstein J Org Chem. 2016 Aug 3;12:1647-748. doi: 10.3762/bjoc.12.162. eCollection 2016.

本文引用的文献

1
A novel strategy for the construction of substituted benzoxazoles via a tandem oxidative process.
Chem Commun (Camb). 2013 Dec 4;49(93):10968-70. doi: 10.1039/c3cc46375c.
2
Oxidative 1,2-difunctionalization of activated alkenes with benzylic C(sp3)-H bonds and aryl C(sp2)-H bonds.
Chem Commun (Camb). 2013 Nov 28;49(92):10817-9. doi: 10.1039/c3cc45861j.
3
Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process.
Beilstein J Org Chem. 2013 Aug 21;9:1718-23. doi: 10.3762/bjoc.9.197. eCollection 2013.
4
Carbon-sulfur bond formation catalyzed by [Pd(IPr*(OMe))(cin)Cl] (cin = cinnamyl).
J Org Chem. 2013 Sep 20;78(18):9303-8. doi: 10.1021/jo401492n. Epub 2013 Sep 10.
6
Cu(II)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides.
Chem Commun (Camb). 2013 May 7;49(35):3640-2. doi: 10.1039/c3cc41188e. Epub 2013 Mar 25.
7
Direct selective oxidative cross-coupling of simple alkanes with heteroarenes.
Angew Chem Int Ed Engl. 2013 Mar 11;52(11):3267-71. doi: 10.1002/anie.201209584. Epub 2013 Jan 31.
8
An iron catalyst for oxidation of alkyl C-H bonds showing enhanced selectivity for methylenic sites.
Chemistry. 2013 Feb 4;19(6):1908-13. doi: 10.1002/chem.201203281. Epub 2012 Dec 19.
9
Transition metal-free direct C-H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes.
Chem Commun (Camb). 2012 Nov 28;48(92):11307-9. doi: 10.1039/c2cc36711d.
10
CuI controlled C-C and C-N bond formation of heteroaromatics through C(sp3)-H activation.
Org Lett. 2012 Nov 2;14(21):5546-9. doi: 10.1021/ol302640e. Epub 2012 Oct 16.

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