Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated,...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2021-12, Vol.23 (24), p.9371-9375
Main Authors: Leech, Matthew C, Petti, Alessia, Tanbouza, Nour, Mastrodonato, Andrea, Goodall, Iain C A, Ollevier, Thierry, Dobbs, Adrian P, Lam, Kevin
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863
cites cdi_FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863
container_end_page 9375
container_issue 24
container_start_page 9371
container_title Organic letters
container_volume 23
creator Leech, Matthew C
Petti, Alessia
Tanbouza, Nour
Mastrodonato, Andrea
Goodall, Iain C A
Ollevier, Thierry
Dobbs, Adrian P
Lam, Kevin
description A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.
doi_str_mv 10.1021/acs.orglett.1c03475
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2604464776</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2604464776</sourcerecordid><originalsourceid>FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863</originalsourceid><addsrcrecordid>eNo9kNtKAzEQhoMotlafQJBcerM1xz14V4qHQqXg4Tpkk1mJ7G7qJgvWp3dL117N8PN_M_AhdE3JnBJG77QJc9991hDjnBrCRSZP0JRKxpOMSHZ63FMyQRchfBFCh6Q4RxMuckHzLJui1aL11hm8-XFWR-db7Cu8aFzrI8RO__oawj1e4BdXW6xbi990BfjV9xFw9HgVvNnp1lkIl-is0nWAq3HO0Mfjw_vyOVlvnlbLxToxXJKY0NLYQkBZgjWclToDaoZIUsMKluciN6ySRZ6mVKYi05UuwMpMGDClYDZP-QzdHu5uO__dQ4iqccFAXesWfB8US4kQA5rtq_xQNZ0PoYNKbTvX6G6nKFF7h2pwqEaHanQ4UDfjg75swB6Zf2n8D0BNcJQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2604464776</pqid></control><display><type>article</type><title>Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Leech, Matthew C ; Petti, Alessia ; Tanbouza, Nour ; Mastrodonato, Andrea ; Goodall, Iain C A ; Ollevier, Thierry ; Dobbs, Adrian P ; Lam, Kevin</creator><creatorcontrib>Leech, Matthew C ; Petti, Alessia ; Tanbouza, Nour ; Mastrodonato, Andrea ; Goodall, Iain C A ; Ollevier, Thierry ; Dobbs, Adrian P ; Lam, Kevin</creatorcontrib><description>A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c03475</identifier><identifier>PMID: 34841877</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2021-12, Vol.23 (24), p.9371-9375</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863</citedby><cites>FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863</cites><orcidid>0000-0002-9729-0918 ; 0000-0003-3524-2897 ; 0000-0003-2212-2052 ; 0000-0003-1481-9212 ; 0000-0002-6084-7954</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/34841877$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Leech, Matthew C</creatorcontrib><creatorcontrib>Petti, Alessia</creatorcontrib><creatorcontrib>Tanbouza, Nour</creatorcontrib><creatorcontrib>Mastrodonato, Andrea</creatorcontrib><creatorcontrib>Goodall, Iain C A</creatorcontrib><creatorcontrib>Ollevier, Thierry</creatorcontrib><creatorcontrib>Dobbs, Adrian P</creatorcontrib><creatorcontrib>Lam, Kevin</creatorcontrib><title>Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNo9kNtKAzEQhoMotlafQJBcerM1xz14V4qHQqXg4Tpkk1mJ7G7qJgvWp3dL117N8PN_M_AhdE3JnBJG77QJc9991hDjnBrCRSZP0JRKxpOMSHZ63FMyQRchfBFCh6Q4RxMuckHzLJui1aL11hm8-XFWR-db7Cu8aFzrI8RO__oawj1e4BdXW6xbi990BfjV9xFw9HgVvNnp1lkIl-is0nWAq3HO0Mfjw_vyOVlvnlbLxToxXJKY0NLYQkBZgjWclToDaoZIUsMKluciN6ySRZ6mVKYi05UuwMpMGDClYDZP-QzdHu5uO__dQ4iqccFAXesWfB8US4kQA5rtq_xQNZ0PoYNKbTvX6G6nKFF7h2pwqEaHanQ4UDfjg75swB6Zf2n8D0BNcJQ</recordid><startdate>20211217</startdate><enddate>20211217</enddate><creator>Leech, Matthew C</creator><creator>Petti, Alessia</creator><creator>Tanbouza, Nour</creator><creator>Mastrodonato, Andrea</creator><creator>Goodall, Iain C A</creator><creator>Ollevier, Thierry</creator><creator>Dobbs, Adrian P</creator><creator>Lam, Kevin</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9729-0918</orcidid><orcidid>https://orcid.org/0000-0003-3524-2897</orcidid><orcidid>https://orcid.org/0000-0003-2212-2052</orcidid><orcidid>https://orcid.org/0000-0003-1481-9212</orcidid><orcidid>https://orcid.org/0000-0002-6084-7954</orcidid></search><sort><creationdate>20211217</creationdate><title>Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides</title><author>Leech, Matthew C ; Petti, Alessia ; Tanbouza, Nour ; Mastrodonato, Andrea ; Goodall, Iain C A ; Ollevier, Thierry ; Dobbs, Adrian P ; Lam, Kevin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leech, Matthew C</creatorcontrib><creatorcontrib>Petti, Alessia</creatorcontrib><creatorcontrib>Tanbouza, Nour</creatorcontrib><creatorcontrib>Mastrodonato, Andrea</creatorcontrib><creatorcontrib>Goodall, Iain C A</creatorcontrib><creatorcontrib>Ollevier, Thierry</creatorcontrib><creatorcontrib>Dobbs, Adrian P</creatorcontrib><creatorcontrib>Lam, Kevin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leech, Matthew C</au><au>Petti, Alessia</au><au>Tanbouza, Nour</au><au>Mastrodonato, Andrea</au><au>Goodall, Iain C A</au><au>Ollevier, Thierry</au><au>Dobbs, Adrian P</au><au>Lam, Kevin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2021-12-17</date><risdate>2021</risdate><volume>23</volume><issue>24</issue><spage>9371</spage><epage>9375</epage><pages>9371-9375</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.</abstract><cop>United States</cop><pmid>34841877</pmid><doi>10.1021/acs.orglett.1c03475</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-9729-0918</orcidid><orcidid>https://orcid.org/0000-0003-3524-2897</orcidid><orcidid>https://orcid.org/0000-0003-2212-2052</orcidid><orcidid>https://orcid.org/0000-0003-1481-9212</orcidid><orcidid>https://orcid.org/0000-0002-6084-7954</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2021-12, Vol.23 (24), p.9371-9375
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2604464776
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T13%3A46%3A33IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Anodic%20Oxidation%20of%20Aminotetrazoles:%20A%20Mild%20and%20Safe%20Route%20to%20Isocyanides&rft.jtitle=Organic%20letters&rft.au=Leech,%20Matthew%20C&rft.date=2021-12-17&rft.volume=23&rft.issue=24&rft.spage=9371&rft.epage=9375&rft.pages=9371-9375&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c03475&rft_dat=%3Cproquest_cross%3E2604464776%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c350t-1bcd94ebbedc32ba7e1cbcd51c2928848c2f5986615647afa9ed574cecb42d863%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2604464776&rft_id=info:pmid/34841877&rfr_iscdi=true