Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent

C-N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp 3 )-H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are comme...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2024-03, Vol.6 (27), p.375-378
Hauptverfasser:	Hooson, James F, Tran, Hai N, Bian, Kang-Jie, West, Julian G
Format:	Artikel
Sprache:	eng
Schlagworte:	Agrochemicals Catalysis Constraining Hydrogen atoms Manganese Reagents Substrates
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	378
container_issue	27
container_start_page	375
container_title	Chemical communications (Cambridge, England)
container_volume	6
creator	Hooson, James F Tran, Hai N Bian, Kang-Jie West, Julian G
description	C-N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp 3 )-H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are commercially available, the experimental procedure is simple, and we can use the C-H donor substrate as the limiting reagent, a challenge for many C-H azidation methods. Preliminary experiments are consistent with a hydrogen atom transfer (HAT)/radical ligand transfer (RLT) radical cascade mechanism and a wide variety of substrates can be azidated in moderate to high yields. C(sp 3 )-H bonds can be directly azidated using simple iron and manganese catalysts and commercial Selectfluor and TMSN 3 as reagents.
doi_str_mv	10.1039/d3cc04728h
format	Article
fullrecord	<record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmed_primary_38477139</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3003893651</sourcerecordid><originalsourceid>FETCH-LOGICAL-c337t-ea6d84d90932cd3a86fb0f22b8b8ec8f2449a0d60c9dad4ef8d7082ddcbe74fc3</originalsourceid><addsrcrecordid>eNpdkctLxDAQxoMo7rp68a4UvKxiNe2kbXKU-lhhYQ8qeCtpku5m6cskPax_vd2HKziXGb758TF8g9B5gO8CDOxeghCYJCFdHKBhADHxI0I_D9dzxPwESDRAJ9YucV9BRI_RAChJkgDYEM3edNWW6tYT3PFy5bTw0rFtr_2Jx7-15E43tddZXc89t1Be2uuyqRvjcbsRSl1pt94axeeqdqfoqOClVWe7PkIfz0_v6cSfzl5e04epLwAS5yseS0okwwxCIYHTuMhxEYY5zakStAgJYRzLGAsmuSSqoDLBNJRS5CohhYARGm99W9N8dcq6rNJWqLLktWo6m4UsimMaYAo9evUPXTadqfvrMsAYKIM4CnrqZksJ01hrVJG1RlfcrLIAZ-uYs0dI003Mkx6-3Fl2eaXkHv3NtQcutoCxYr_9-xP8ACTogI8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3003893651</pqid></control><display><type>article</type><title>Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Hooson, James F ; Tran, Hai N ; Bian, Kang-Jie ; West, Julian G</creator><creatorcontrib>Hooson, James F ; Tran, Hai N ; Bian, Kang-Jie ; West, Julian G</creatorcontrib><description>C-N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp 3 )-H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are commercially available, the experimental procedure is simple, and we can use the C-H donor substrate as the limiting reagent, a challenge for many C-H azidation methods. Preliminary experiments are consistent with a hydrogen atom transfer (HAT)/radical ligand transfer (RLT) radical cascade mechanism and a wide variety of substrates can be azidated in moderate to high yields. C(sp 3 )-H bonds can be directly azidated using simple iron and manganese catalysts and commercial Selectfluor and TMSN 3 as reagents.</description><identifier>ISSN: 1359-7345</identifier><identifier>ISSN: 1364-548X</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d3cc04728h</identifier><identifier>PMID: 38477139</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Agrochemicals ; Catalysis ; Constraining ; Hydrogen atoms ; Manganese ; Reagents ; Substrates</subject><ispartof>Chemical communications (Cambridge, England), 2024-03, Vol.6 (27), p.375-378</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-ea6d84d90932cd3a86fb0f22b8b8ec8f2449a0d60c9dad4ef8d7082ddcbe74fc3</citedby><cites>FETCH-LOGICAL-c337t-ea6d84d90932cd3a86fb0f22b8b8ec8f2449a0d60c9dad4ef8d7082ddcbe74fc3</cites><orcidid>0000-0003-2486-5220 ; 0000-0002-3715-7883</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38477139$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hooson, James F</creatorcontrib><creatorcontrib>Tran, Hai N</creatorcontrib><creatorcontrib>Bian, Kang-Jie</creatorcontrib><creatorcontrib>West, Julian G</creatorcontrib><title>Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>C-N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp 3 )-H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are commercially available, the experimental procedure is simple, and we can use the C-H donor substrate as the limiting reagent, a challenge for many C-H azidation methods. Preliminary experiments are consistent with a hydrogen atom transfer (HAT)/radical ligand transfer (RLT) radical cascade mechanism and a wide variety of substrates can be azidated in moderate to high yields. C(sp 3 )-H bonds can be directly azidated using simple iron and manganese catalysts and commercial Selectfluor and TMSN 3 as reagents.</description><subject>Agrochemicals</subject><subject>Catalysis</subject><subject>Constraining</subject><subject>Hydrogen atoms</subject><subject>Manganese</subject><subject>Reagents</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkctLxDAQxoMo7rp68a4UvKxiNe2kbXKU-lhhYQ8qeCtpku5m6cskPax_vd2HKziXGb758TF8g9B5gO8CDOxeghCYJCFdHKBhADHxI0I_D9dzxPwESDRAJ9YucV9BRI_RAChJkgDYEM3edNWW6tYT3PFy5bTw0rFtr_2Jx7-15E43tddZXc89t1Be2uuyqRvjcbsRSl1pt94axeeqdqfoqOClVWe7PkIfz0_v6cSfzl5e04epLwAS5yseS0okwwxCIYHTuMhxEYY5zakStAgJYRzLGAsmuSSqoDLBNJRS5CohhYARGm99W9N8dcq6rNJWqLLktWo6m4UsimMaYAo9evUPXTadqfvrMsAYKIM4CnrqZksJ01hrVJG1RlfcrLIAZ-uYs0dI003Mkx6-3Fl2eaXkHv3NtQcutoCxYr_9-xP8ACTogI8</recordid><startdate>20240328</startdate><enddate>20240328</enddate><creator>Hooson, James F</creator><creator>Tran, Hai N</creator><creator>Bian, Kang-Jie</creator><creator>West, Julian G</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2486-5220</orcidid><orcidid>https://orcid.org/0000-0002-3715-7883</orcidid></search><sort><creationdate>20240328</creationdate><title>Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent</title><author>Hooson, James F ; Tran, Hai N ; Bian, Kang-Jie ; West, Julian G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-ea6d84d90932cd3a86fb0f22b8b8ec8f2449a0d60c9dad4ef8d7082ddcbe74fc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Agrochemicals</topic><topic>Catalysis</topic><topic>Constraining</topic><topic>Hydrogen atoms</topic><topic>Manganese</topic><topic>Reagents</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hooson, James F</creatorcontrib><creatorcontrib>Tran, Hai N</creatorcontrib><creatorcontrib>Bian, Kang-Jie</creatorcontrib><creatorcontrib>West, Julian G</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hooson, James F</au><au>Tran, Hai N</au><au>Bian, Kang-Jie</au><au>West, Julian G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2024-03-28</date><risdate>2024</risdate><volume>6</volume><issue>27</issue><spage>375</spage><epage>378</epage><pages>375-378</pages><issn>1359-7345</issn><issn>1364-548X</issn><eissn>1364-548X</eissn><abstract>C-N bonds play a critical role in pharmaceutical, agrochemical, and materials sciences, necessitating ever-better methods to forge this linkage. Here we report a simple procedure for direct C(sp 3 )-H azidation using iron or manganese catalysis and a nucleophilic azide source. All reagents are commercially available, the experimental procedure is simple, and we can use the C-H donor substrate as the limiting reagent, a challenge for many C-H azidation methods. Preliminary experiments are consistent with a hydrogen atom transfer (HAT)/radical ligand transfer (RLT) radical cascade mechanism and a wide variety of substrates can be azidated in moderate to high yields. C(sp 3 )-H bonds can be directly azidated using simple iron and manganese catalysts and commercial Selectfluor and TMSN 3 as reagents.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38477139</pmid><doi>10.1039/d3cc04728h</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-2486-5220</orcidid><orcidid>https://orcid.org/0000-0002-3715-7883</orcidid></addata></record>
fulltext	fulltext
identifier	ISSN: 1359-7345
ispartof	Chemical communications (Cambridge, England), 2024-03, Vol.6 (27), p.375-378
issn	1359-7345 1364-548X 1364-548X
language	eng
recordid	cdi_pubmed_primary_38477139
source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Agrochemicals Catalysis Constraining Hydrogen atoms Manganese Reagents Substrates
title	Simple, catalytic C(sp)-H azidation using the C-H donor as the limiting reagent
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T12%3A40%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Simple,%20catalytic%20C(sp)-H%20azidation%20using%20the%20C-H%20donor%20as%20the%20limiting%20reagent&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Hooson,%20James%20F&rft.date=2024-03-28&rft.volume=6&rft.issue=27&rft.spage=375&rft.epage=378&rft.pages=375-378&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d3cc04728h&rft_dat=%3Cproquest_pubme%3E3003893651%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3003893651&rft_id=info:pmid/38477139&rfr_iscdi=true