Ni(II) Salt-catalyzed Direct Aryl Thioetherification of 1-Naphthylamine and Its Derivative with Disulfides
The direct C-H aryl thioetherification of 1-naphthylamine and its derivative with diaryl disulfides was developed with a Ni(II) salt catalytic system under air. The protocol was compatible with a wide range of functional groups. 1-Naphthylamine and 1,2,3,4-tetrahydro-1-naphthylamine were converted i...
Saved in:
| Published in | Chemistry letters Vol. 51; no. 6; pp. 669 - 672 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Oxford Univ Press
05.06.2022
|
| Subjects | |
| Online Access | Get more information |
Cover
Loading…
| Abstract | The direct C-H aryl thioetherification of 1-naphthylamine and its derivative with diaryl disulfides was developed with a Ni(II) salt catalytic system under air. The protocol was compatible with a wide range of functional groups. 1-Naphthylamine and 1,2,3,4-tetrahydro-1-naphthylamine were converted into various aryl sulfide compounds under standard conditions. The application of the proposed methodology to prepare some highly-functionalized small molecules as building blocks for bioactive compounds was explored. Control experiments revealed the Ni(II)/Ni(IV) cyclic mechanism of the catalytic system. |
|---|---|
| AbstractList | The direct C-H aryl thioetherification of 1-naphthylamine and its derivative with diaryl disulfides was developed with a Ni(II) salt catalytic system under air. The protocol was compatible with a wide range of functional groups. 1-Naphthylamine and 1,2,3,4-tetrahydro-1-naphthylamine were converted into various aryl sulfide compounds under standard conditions. The application of the proposed methodology to prepare some highly-functionalized small molecules as building blocks for bioactive compounds was explored. Control experiments revealed the Ni(II)/Ni(IV) cyclic mechanism of the catalytic system. |
| Author | Zhang, Le Liu, Tian Liu, Kaixuan Zhang, Nan Xu, Youjun Jiang, Chunfeng |
| Author_xml | – sequence: 1 givenname: Chunfeng surname: Jiang fullname: Jiang, Chunfeng organization: Liaoning Inst Sci & Technol, Benxi 117004, Peoples R China – sequence: 2 givenname: Kaixuan surname: Liu fullname: Liu, Kaixuan organization: Liaoning Inst Sci & Technol, Benxi 117004, Peoples R China – sequence: 3 givenname: Le surname: Zhang fullname: Zhang, Le organization: Liaoning Inst Sci & Technol, Benxi 117004, Peoples R China – sequence: 4 givenname: Tian surname: Liu fullname: Liu, Tian organization: Liaoning Inst Sci & Technol, Benxi 117004, Peoples R China – sequence: 5 givenname: Nan surname: Zhang fullname: Zhang, Nan organization: Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China – sequence: 6 givenname: Youjun surname: Xu fullname: Xu, Youjun email: xuyoujun@syphu.edu.cn organization: Liaoning Inst Sci & Technol, Benxi 117004, Peoples R China |
| BookMark | eNqNj8tuwjAURK2KSgXaRf_Ay1aVqR9x4ixR6CMSoovSNTL2tWJkEpQYUPr1TR8f0NXM4pyRZoJGdVMDQreMzhhP0kcTZpxTlqoLNGYiUYRmTI7QmIo0JRnl_ApNum5HKVW54GO0W_m7srzH7zpEYnTUof8Eixe-BRPxvO0DXle-gVhB650fCN_UuHGYkZU-VLHqg977GrCuLS5jhxcDdxqoE-Czj9Ww1B2D8xa6a3TpdOjg5i-n6OP5aV28kuXbS1nMl8TwNIkEmDLS2MwJIyDfCptCAsYqo6wTcqutZVIlQnBtHYDUigumBcsUSJfnacanSP3unmHbuM54qA1sDq3f67bffD8XUjCaDY2JwsefS0VzrOOgPvxf5V_GEHBD |
| Cites_doi | 10.1021/np400355h 10.1246/cl.150024 10.1038/s42004-022-00633-3 10.1021/jacs.7b03548 10.1002/chem.202001318 10.1039/c8cc02158a 10.1021/acs.orglett.5b00337 10.1039/c4cc10431e 10.1021/ol201930e 10.1021/jm401375q 10.1039/c4cc10446c 10.1016/j.bmc.2011.12.003 10.1016/j.trechm.2019.06.002 10.1021/ja401344e 10.1021/acscatal.1c02516 10.1039/c7qo01016h 10.1021/np400284z 10.1039/c5ob00149h 10.1021/jo502274t 10.1021/jm900296e |
| ContentType | Journal Article |
| DBID | 17B 1KM 1KN AHQBO BLEPL DTL EGQ |
| DOI | 10.1246/cl.220168 |
| DatabaseName | Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2022 Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) |
| DatabaseTitle | Web of Science |
| DatabaseTitleList | Web of Science |
| Database_xml | – sequence: 1 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1348-0715 |
| EndPage | 672 |
| ExternalDocumentID | 000835310700013 |
| FullText_t_NoSnippeting | true |
| GrantInformation_xml | – fundername: Natura l Science Foundat ion of Liaon ing Province; Natural Science Foundation of Liaoning Province grantid: 2021 -MS -310 – fundername: Program for L iaon ing Innovative Talentsin University grantid: LR2020028 – fundername: Scient ific Research Project o f Educat ion Department o f Liaon ing Province grantid: L2020 lkyqn- 05 |
| GroupedDBID | -~X 0R~ 17B 1KM 1KN 29B 53G 5GY 6J9 AAUAY ABCQX ABDFA ABEFU ABEJV ABGNP ABJNI ABVGC ABXVV ABZEH ACGFO ACIWK ACNCT ADIPN ADNBA ADVOB AENEX AGORE AJNCP ALMA_UNASSIGNED_HOLDINGS BCRHZ BLEPL CS3 DTL DU5 EBS EJD GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE H13 KOP L7B OJZSN OK1 OWPYF OXVGQ P2P ROX SJN TWZ UPT ~02 |
| ID | FETCH-LOGICAL-c264t-e18c5cd7f3c3e9b3d6e4ecd8c8df35badd1584332adfee5a8231a3178e5f99672 |
| ISICitedReferencesCount | 0 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000835310700013 |
| ISSN | 0366-7022 |
| IngestDate | Fri Aug 29 16:02:23 EDT 2025 Mon Jul 21 06:52:47 EDT 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 6 |
| Keywords | FUNCTIONALIZATION ALKYLATION THIOLATION C-H aryl thioetherification DIRECT SULFENYLATION 1,2,3,4-Tetrahydro-1-naphthylamine Ni(II) salt catalytic system C-H BONDS |
| Language | English |
| LinkModel | OpenURL |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c264t-e18c5cd7f3c3e9b3d6e4ecd8c8df35badd1584332adfee5a8231a3178e5f99672 |
| PageCount | 4 |
| ParticipantIDs | webofscience_primary_000835310700013CitationCount webofscience_primary_000835310700013 |
| PublicationCentury | 2000 |
| PublicationDate | 2022-06-05 |
| PublicationDateYYYYMMDD | 2022-06-05 |
| PublicationDate_xml | – month: 06 year: 2022 text: 2022-06-05 day: 05 |
| PublicationDecade | 2020 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD |
| PublicationTitle | Chemistry letters |
| PublicationTitleAbbrev | CHEM LETT |
| PublicationYear | 2022 |
| Publisher | Oxford Univ Press |
| Publisher_xml | – name: Oxford Univ Press |
| References | Kamal, A (WOS:000299496100030) 2012; 20 Yang, K (WOS:000349325400022) 2015; 51 (000835310700013.8) 2016 Le Grand, B (WOS:000268139900013) 2009; 52 Lin, C (WOS:000350841300068) 2015; 17 Omer, HM (WOS:000417342500007) 2017; 139 Iwasaki, M (WOS:000346038300004) 2014; 79 Bontemps, N (WOS:000330331200037) 2013; 76 Reddy, VP (WOS:000355985800018) 2015; 13 Rosen, H (WOS:000078324400047) 1999; 283 Xiong, YS (WOS:000428091500013) 2018; 5 Castro, LCM (WOS:000352328700001) 2015; 44 MARCINCALLEFEBVRE, A (WOS:A1981LU64400024) 1981; 24 Woo, CM (WOS:000322562900002) 2013; 76 Aihara, Y (WOS:000317548400021) 2013; 135 Yan, SY (WOS:000350212600028) 2015; 51 Ilardi, EA (WOS:000334572000002) 2014; 57 Roy, S (WOS:000430022100024) 2018; 54 Rhlee, JH (WOS:000750819500001) 2022; 5 Zhao, YS (WOS:000294703900025) 2011; 13 Massignan, L (WOS:000697346200032) 2021; 11 Khake, SM (WOS:000521129900009) 2019; 1 Zhang, SK (WOS:000552824300001) 2020; 26 Maslak, P (WOS:A1996TV70600026) 1996; 118 |
| References_xml | – volume: 118 start-page: 1471 year: 1996 ident: WOS:A1996TV70600026 article-title: Optical properties of spiroconjugated charge-transfer dyes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 76 start-page: 1238 year: 2013 ident: WOS:000322562900002 article-title: Insights into Lomaiviticin Biosynthesis. Isolation and Structure Elucidation of (-)-Homoseongomycin publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np400355h – volume: 44 start-page: 410 year: 2015 ident: WOS:000352328700001 article-title: Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.150024 – volume: 5 start-page: ARTN 13 year: 2022 ident: WOS:000750819500001 article-title: Synthesis of α,β-unsaturated ketones through nickel-catalysed aldehyde-free hydroacylation of alkynes publication-title: COMMUNICATIONS CHEMISTRY doi: 10.1038/s42004-022-00633-3 – volume: 139 start-page: 9909 year: 2017 ident: WOS:000417342500007 article-title: Computational Study of Ni-Catalyzed C-H Functionalization: Factors That Control the Competition of Oxidative Addition and Radical Pathways publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03548 – volume: 26 start-page: 10936 year: 2020 ident: WOS:000552824300001 article-title: Evolution of High-Valent Nickela-Electrocatalyzed C-H Activation: From Cross(-Electrophile)-Couplings to Electrooxidative C-H Transformations publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.202001318 – volume: 54 start-page: 3899 year: 2018 ident: WOS:000430022100024 article-title: Copper-mediated regioselective C-H etherification of naphthylamides with arylboronic acids using water as an oxygen source publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c8cc02158a – volume: 17 start-page: 1328 year: 2015 ident: WOS:000350841300068 article-title: Direct ortho-Thiolation of Arenes and Alkenes by Nickel Catalysis publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b00337 – volume: 51 start-page: 3582 year: 2015 ident: WOS:000349325400022 article-title: Nickel-catalyzed and benzoic acid-promoted direct sulfenylation of unactivated arenes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc10431e – volume: 13 start-page: 4850 year: 2011 ident: WOS:000294703900025 article-title: Palladium-Catalyzed Alkylation of ortho-C(sp2)-H Bonds of Benzylamide Substrates with Alkyl Halides publication-title: ORGANIC LETTERS doi: 10.1021/ol201930e – volume: 57 start-page: 2832 year: 2014 ident: WOS:000334572000002 article-title: Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm401375q – year: 2016 ident: 000835310700013.8 publication-title: PCT Int. Appl. – volume: 51 start-page: 4069 year: 2015 ident: WOS:000350212600028 article-title: Nickel-catalyzed thiolation of unactivated aryl C-H bonds: efficient access to diverse aryl sulfides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc10446c – volume: 20 start-page: 789 year: 2012 ident: WOS:000299496100030 article-title: Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents publication-title: BIOORGANIC & MEDICINAL CHEMISTRY doi: 10.1016/j.bmc.2011.12.003 – volume: 1 start-page: 524 year: 2019 ident: WOS:000521129900009 article-title: Chelation-Assisted Nickel-Catalyzed C-H Functionalizations publication-title: TRENDS IN CHEMISTRY doi: 10.1016/j.trechm.2019.06.002 – volume: 135 start-page: 5308 year: 2013 ident: WOS:000317548400021 article-title: Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja401344e – volume: 11 start-page: 11639 year: 2021 ident: WOS:000697346200032 article-title: Manganaelectro-Catalyzed Azine C-H Arylations and C-H Alkylations by Assistance of Weakly Coordinating Amides publication-title: ACS CATALYSIS doi: 10.1021/acscatal.1c02516 – volume: 24 start-page: 889 year: 1981 ident: WOS:A1981LU64400024 article-title: (PHENYLTHIO)PHENYLAMINE DERIVATIVES AS POTENTIAL ANTI-INFLAMMATORY COMPOUNDS publication-title: JOURNAL OF MEDICINAL CHEMISTRY – volume: 5 start-page: 982 year: 2018 ident: WOS:000428091500013 article-title: Copper-catalyzed peri-selective direct sulfenylation of 1-naphthylamines with disulfides publication-title: ORGANIC CHEMISTRY FRONTIERS doi: 10.1039/c7qo01016h – volume: 76 start-page: 1801 year: 2013 ident: WOS:000330331200037 article-title: Additional Cytotoxic Pyridoacridine Alkaloids from the Ascidian Cystodytes violatinctus and Biogenetic Considerations publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np400284z – volume: 283 start-page: 703 year: 1999 ident: WOS:000078324400047 article-title: Reduced immunotoxicity and preservation of antibacterial activity in a releasable side-chain carbapenem antibiotic publication-title: SCIENCE – volume: 13 start-page: 6803 year: 2015 ident: WOS:000355985800018 article-title: Nickel-catalyzed synthesis of diarylsulfides and sulfones via C-H bond functionalization of arylamides publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c5ob00149h – volume: 79 start-page: 11330 year: 2014 ident: WOS:000346038300004 article-title: Palladium-Catalyzed pen-Selective Chalcogenation of Naphthylamines with Diaryl Disulfides and Diselenides via C-H Bond Cleavage publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo502274t – volume: 52 start-page: 4149 year: 2009 ident: WOS:000268139900013 article-title: Na+ Currents in Cardioprotection: Better to Be Late publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm900296e |
| SSID | ssj0008932 |
| Score | 2.350903 |
| Snippet | The direct C-H aryl thioetherification of 1-naphthylamine and its derivative with diaryl disulfides was developed with a Ni(II) salt catalytic system under... |
| Source | Web of Science |
| SourceID | webofscience |
| SourceType | Enrichment Source Index Database |
| StartPage | 669 |
| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Ni(II) Salt-catalyzed Direct Aryl Thioetherification of 1-Naphthylamine and Its Derivative with Disulfides |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000835310700013 |
| Volume | 51 |
| WOS | 000835310700013 |
| WOSCitedRecordID | wos000835310700013 |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3JTsMwELUKHOCCWEXZ5AMHEEppajtJj6iAKEsvFIkbih1bBFUtggQBP8LvMl6adOFQuERVlCZq39PMm8ksCB2A_QOvoAKPUN2SEzUjj-tG3WbIGIvrilBupn12gst7evXAHiqV75GqpTzjNfH1a1_Jf1CFc4Cr7pL9A7LFTeEEfAZ84QgIw3EmjDup1odtHdnfxb3MM7mYzy_QkNaSHZ--fprVnAPT1qurggqF6Hud-OUJYAJKaKVp6oKzNzBAr2bh2bu0Odqz9C3vqTRxtYbDoQbDPXHHPdMPVBYipi4B3XrK-0o6v6grftLcVm-kH3nJyCJffSMnLuwOeetSEhDN6qwEKwPYstVxrJDENmkFXli3rcg1aW0uoZHuo2KjRtlNoU2nLGxgN7s4Zx3YvT9TfqBhBiCLXq0BAsfu7RmftT3hA4vKRKtJQfOGRh3PoTkIP7Tuvr4tHDxIPPtyyv0WN7AKnnlSPPFXHWM0S3cFLbtgA59a5qyiiuyvocUCu3X03EkP2-0jPM4ebNmDNXvwNHvwQOEJ9mBgDwb24JI9WLMHl-zZQPcX593Wpee2b3gCRHLmST8STCShIoLIJidJIKnUkySiRBHGwS_6IF4JacSJkpLF-n1yDGo0kkxBEB02NtF8f9CXWwjTRBARBfAdX9GEBZwLP2b1hIIYCimPquhg9M96fLGDVh4nwKgif5bLWm64vR7qkG3PdusdtFQSeRctKLAQcg_kZsb3Dfg_zkOAnw |
| linkProvider | Clarivate |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Ni%28II%29+Salt-catalyzed+Direct+Aryl+Thioetherification+of+1-Naphthylamine+and+Its+Derivative+with+Disulfides&rft.jtitle=Chemistry+letters&rft.au=Jiang%2C+Chunfeng&rft.au=Liu%2C+Kaixuan&rft.au=Zhang%2C+Le&rft.au=Liu%2C+Tian&rft.date=2022-06-05&rft.pub=Oxford+Univ+Press&rft.issn=0366-7022&rft.eissn=1348-0715&rft.volume=51&rft.issue=6&rft.spage=669&rft.epage=672&rft_id=info:doi/10.1246%2Fcl.220168&rft.externalDBID=n%2Fa&rft.externalDocID=000835310700013 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0366-7022&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0366-7022&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0366-7022&client=summon |