<?xml version="1.0" encoding="utf-8"?>
<TEI xmlns="http://www.tei-c.org/ns/1.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:hal="http://hal.archives-ouvertes.fr/" xmlns:gml="http://www.opengis.net/gml/3.3/" xmlns:gmlce="http://www.opengis.net/gml/3.3/ce" version="1.1" xsi:schemaLocation="http://www.tei-c.org/ns/1.0 http://api.archives-ouvertes.fr/documents/aofr-sword.xsd">
  <teiHeader>
    <fileDesc>
      <titleStmt>
        <title>HAL TEI export of hal-03841084</title>
      </titleStmt>
      <publicationStmt>
        <distributor>CCSD</distributor>
        <availability status="restricted">
          <licence target="https://creativecommons.org/publicdomain/zero/1.0/">CC0 1.0 - Universal</licence>
        </availability>
        <date when="2026-05-25T07:32:12+02:00"/>
      </publicationStmt>
      <sourceDesc>
        <p part="N">HAL API Platform</p>
      </sourceDesc>
    </fileDesc>
  </teiHeader>
  <text>
    <body>
      <listBibl>
        <biblFull>
          <titleStmt>
            <title xml:lang="en">Precise Control of the Site-Selectivity in Ruthenium-Catalyzed C-H Bond Amidations by Cyclic Amides as Powerful Directing Groups</title>
            <author role="crp">
              <persName>
                <forename type="first">Yu-Chao</forename>
                <surname>Yuan</surname>
              </persName>
              <idno type="halauthorid">2536556-0</idno>
              <affiliation ref="#struct-519855"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Qiu-Li</forename>
                <surname>Lu</surname>
              </persName>
              <idno type="halauthorid">2632697-0</idno>
              <affiliation ref="#struct-519855"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Xiao-Tong</forename>
                <surname>Zhu</surname>
              </persName>
              <idno type="halauthorid">2632698-0</idno>
              <affiliation ref="#struct-519855"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Sergio</forename>
                <surname>Posada-Pérez</surname>
              </persName>
              <idno type="halauthorid">2632699-0</idno>
              <affiliation ref="#struct-548220"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Miquel</forename>
                <surname>Solà</surname>
              </persName>
              <idno type="halauthorid">882030-0</idno>
              <affiliation ref="#struct-548220"/>
            </author>
            <author role="crp">
              <persName>
                <forename type="first">Albert</forename>
                <surname>Poater</surname>
              </persName>
              <idno type="halauthorid">202923-0</idno>
              <affiliation ref="#struct-548220"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Thierry</forename>
                <surname>Roisnel</surname>
              </persName>
              <email type="md5">9317198a81adac0b3c18c4cf0829fc0b</email>
              <email type="domain">univ-rennes1.fr</email>
              <idno type="idhal" notation="string">thierry-roisnel</idno>
              <idno type="idhal" notation="numeric">750528</idno>
              <idno type="halauthorid" notation="string">5268-750528</idno>
              <idno type="ORCID">https://orcid.org/0000-0002-6088-4472</idno>
              <affiliation ref="#struct-194938"/>
            </author>
            <author role="crp">
              <persName>
                <forename type="first">Rafael</forename>
                <surname>Gramage-Doria</surname>
              </persName>
              <email type="md5">60ff77b696f1438c04943c6d920f511b</email>
              <email type="domain">univ-rennes1.fr</email>
              <idno type="idhal" notation="string">rafael-gramage-doria</idno>
              <idno type="idhal" notation="numeric">12598</idno>
              <idno type="halauthorid" notation="string">18842-12598</idno>
              <idno type="ORCID">https://orcid.org/0000-0002-0961-4530</idno>
              <idno type="IDREF">https://www.idref.fr/164273719</idno>
              <affiliation ref="#struct-194938"/>
            </author>
            <editor role="depositor">
              <persName>
                <forename>Rafael</forename>
                <surname>Gramage-Doria</surname>
              </persName>
              <email type="md5">60ff77b696f1438c04943c6d920f511b</email>
              <email type="domain">univ-rennes1.fr</email>
            </editor>
            <funder ref="#projanr-54116"/>
            <funder>Y.-C. Y. acknowledges the Science and Technology of XuZhou (KC19042) for financial support. We also thank the Public Experimental Research Center, Xuzhou Medical University, for NMR determination. R. G-D. acknowledges the ANR-JCJC scheme (ANR-19-CE07-0039), CNRS and the University of Rennes 1 for financial support. S. P. P. thanks the Marie Curie fellowship (H2020-MSCA-IF-2020-101020330). A. P. is a Serra Húnter Fellow and thanks ICREA Academia Prize 2019 and Spanish Mineco for project ref. PGC2018-097722-B-I00. A. P. and M. S. thank the Spanish Ministerio de Ciencia e Innovación for projects PID2021-127423NB-I00 and PID2020-13711GB-I00 and the Generalitat de Catalunya for project 2017SGR39.</funder>
          </titleStmt>
          <editionStmt>
            <edition n="v1" type="current">
              <date type="whenSubmitted">2022-11-06 18:00:05</date>
              <date type="whenModified">2026-01-26 08:52:02</date>
              <date type="whenReleased">2022-11-07 16:34:11</date>
              <date type="whenProduced">2023</date>
              <date type="whenEndEmbargoed">2022-11-06</date>
              <ref type="file" target="https://univ-rennes.hal.science/hal-03841084v1/document">
                <date notBefore="2022-11-06"/>
              </ref>
              <ref type="file" subtype="author" n="1" target="https://univ-rennes.hal.science/hal-03841084v1/file/d2qo01434c.pdf" id="file-3841084-3360941">
                <date notBefore="2022-11-06"/>
              </ref>
            </edition>
            <respStmt>
              <resp>contributor</resp>
              <name key="345606">
                <persName>
                  <forename>Rafael</forename>
                  <surname>Gramage-Doria</surname>
                </persName>
                <email type="md5">60ff77b696f1438c04943c6d920f511b</email>
                <email type="domain">univ-rennes1.fr</email>
              </name>
            </respStmt>
          </editionStmt>
          <publicationStmt>
            <distributor>CCSD</distributor>
            <idno type="halId">hal-03841084</idno>
            <idno type="halUri">https://univ-rennes.hal.science/hal-03841084</idno>
            <idno type="halBibtex">yuan:hal-03841084</idno>
            <idno type="halRefHtml">&lt;i&gt;Organic Chemistry Frontiers&lt;/i&gt;, 2023, &lt;a target="_blank" href="https://dx.doi.org/10.1039/D2QO01434C"&gt;&amp;#x27E8;10.1039/D2QO01434C&amp;#x27E9;&lt;/a&gt;</idno>
            <idno type="halRef">Organic Chemistry Frontiers, 2023, &amp;#x27E8;10.1039/D2QO01434C&amp;#x27E9;</idno>
            <availability status="restricted">
              <licence target="https://creativecommons.org/licenses/by/4.0/">CC BY 4.0 - Attribution<ref corresp="#file-3841084-3360941"/></licence>
            </availability>
          </publicationStmt>
          <seriesStmt>
            <idno type="stamp" n="UNIV-RENNES1">Université de Rennes 1</idno>
            <idno type="stamp" n="CNRS">CNRS - Centre national de la recherche scientifique</idno>
            <idno type="stamp" n="INSA-RENNES">Institut National des Sciences Appliquées de Rennes</idno>
            <idno type="stamp" n="ENSC-RENNES">Ecole Nationale Supérieure de Chimie de Rennes</idno>
            <idno type="stamp" n="ISCR">INSTITUT DES SCIENCES CHIMIQUES DE RENNES</idno>
            <idno type="stamp" n="SCR-CD">Sciences Chimiques de Rennes / Centre de Diffractométrie</idno>
            <idno type="stamp" n="ISCR-OMC" corresp="ISCR">Organométalliques : Matériaux et Catalyse</idno>
            <idno type="stamp" n="UR1-SPM">Université de Rennes 1 - UFR Sciences et Propriétés de la Matière</idno>
            <idno type="stamp" n="ISCR-PRATS" corresp="ISCR">Pôle ressources de l'ISCR</idno>
            <idno type="stamp" n="INC-CNRS">Institut de Chimie du CNRS</idno>
            <idno type="stamp" n="UR1-UFR-SPM">UFR SPM Sciences et Propriétés de la Matière</idno>
            <idno type="stamp" n="UR1-HAL">Publications labos UR1 dans HAL-Rennes 1</idno>
            <idno type="stamp" n="UR1-SDLM">UR1 - publications SDLM</idno>
            <idno type="stamp" n="TEST-UR-CSS">TEST Université de Rennes CSS</idno>
            <idno type="stamp" n="UNIV-RENNES">Université de Rennes</idno>
            <idno type="stamp" n="INSA-GROUPE">Groupe INSA</idno>
            <idno type="stamp" n="ANR">ANR</idno>
            <idno type="stamp" n="UR1-MMS">Pôle UnivRennes - Matériaux</idno>
            <idno type="stamp" n="TEST2-HALCNRS">TEST2-HALCNRS</idno>
          </seriesStmt>
          <notesStmt>
            <note type="audience" n="2">International</note>
            <note type="popular" n="0">No</note>
            <note type="peer" n="1">Yes</note>
          </notesStmt>
          <sourceDesc>
            <biblStruct>
              <analytic>
                <title xml:lang="en">Precise Control of the Site-Selectivity in Ruthenium-Catalyzed C-H Bond Amidations by Cyclic Amides as Powerful Directing Groups</title>
                <author role="crp">
                  <persName>
                    <forename type="first">Yu-Chao</forename>
                    <surname>Yuan</surname>
                  </persName>
                  <idno type="halauthorid">2536556-0</idno>
                  <affiliation ref="#struct-519855"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Qiu-Li</forename>
                    <surname>Lu</surname>
                  </persName>
                  <idno type="halauthorid">2632697-0</idno>
                  <affiliation ref="#struct-519855"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Xiao-Tong</forename>
                    <surname>Zhu</surname>
                  </persName>
                  <idno type="halauthorid">2632698-0</idno>
                  <affiliation ref="#struct-519855"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Sergio</forename>
                    <surname>Posada-Pérez</surname>
                  </persName>
                  <idno type="halauthorid">2632699-0</idno>
                  <affiliation ref="#struct-548220"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Miquel</forename>
                    <surname>Solà</surname>
                  </persName>
                  <idno type="halauthorid">882030-0</idno>
                  <affiliation ref="#struct-548220"/>
                </author>
                <author role="crp">
                  <persName>
                    <forename type="first">Albert</forename>
                    <surname>Poater</surname>
                  </persName>
                  <idno type="halauthorid">202923-0</idno>
                  <affiliation ref="#struct-548220"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Thierry</forename>
                    <surname>Roisnel</surname>
                  </persName>
                  <email type="md5">9317198a81adac0b3c18c4cf0829fc0b</email>
                  <email type="domain">univ-rennes1.fr</email>
                  <idno type="idhal" notation="string">thierry-roisnel</idno>
                  <idno type="idhal" notation="numeric">750528</idno>
                  <idno type="halauthorid" notation="string">5268-750528</idno>
                  <idno type="ORCID">https://orcid.org/0000-0002-6088-4472</idno>
                  <affiliation ref="#struct-194938"/>
                </author>
                <author role="crp">
                  <persName>
                    <forename type="first">Rafael</forename>
                    <surname>Gramage-Doria</surname>
                  </persName>
                  <email type="md5">60ff77b696f1438c04943c6d920f511b</email>
                  <email type="domain">univ-rennes1.fr</email>
                  <idno type="idhal" notation="string">rafael-gramage-doria</idno>
                  <idno type="idhal" notation="numeric">12598</idno>
                  <idno type="halauthorid" notation="string">18842-12598</idno>
                  <idno type="ORCID">https://orcid.org/0000-0002-0961-4530</idno>
                  <idno type="IDREF">https://www.idref.fr/164273719</idno>
                  <affiliation ref="#struct-194938"/>
                </author>
              </analytic>
              <monogr>
                <idno type="halJournalId" status="VALID">96733</idno>
                <idno type="issn">2052-4110</idno>
                <idno type="eissn">2052-4129</idno>
                <title level="j">Organic Chemistry Frontiers</title>
                <imprint>
                  <publisher>Royal Society of Chemistry</publisher>
                  <date type="datePub">2023</date>
                  <date type="dateEpub">2022-11-05</date>
                </imprint>
              </monogr>
              <idno type="doi">10.1039/D2QO01434C</idno>
            </biblStruct>
          </sourceDesc>
          <profileDesc>
            <langUsage>
              <language ident="en">English</language>
            </langUsage>
            <textClass>
              <classCode scheme="halDomain" n="chim.orga">Chemical Sciences/Organic chemistry</classCode>
              <classCode scheme="halDomain" n="chim.cata">Chemical Sciences/Catalysis</classCode>
              <classCode scheme="halTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halOldTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halTreeTypology" n="ART">Journal articles</classCode>
            </textClass>
            <abstract xml:lang="en">
              <p>Selective C-H functionalizations aiming at the formation of new C-N bonds is of paramount importance in the context of step-and atom-economy methodologies in organic synthesis. Although the implementation of noble metal catalysts is prevalent, more benign cobalt pre-catalysts have recently appeared promising. However, they sometimes feature selectivity issues that limits its applicability in late-stage functionalization. Herein, we report on a highly reactive ruthenium-based catalytic system displaying excellent levels of mono-, regio-and site-selectivity exploiting a series of biologically-relevant cyclic amides as weak directing groups. The use of dioxazolone derivatives as the amidating reagent overcomes the issues encountered in the use of unstable azide derivatives for such transformations and it enables to perform these reactions under very mild reaction conditions (air, 40 o C). Moreover, a combination of deuteration experiments and a comparative study with different types of directing groups highlight the relevance of weak amide directing groups for enabling formation of six-membered cycloruthenate intermediates in key elementary steps of the catalytic cycle. In addition, DFT computational calculations were carried out for the first time for studying ruthenium-catalyzed C-N bond-forming processes via C-H activation assisted by weak directing groups, thereby elucidating the origin of the regio-and site-selectivity.</p>
            </abstract>
          </profileDesc>
        </biblFull>
      </listBibl>
    </body>
    <back>
      <listOrg type="structures">
        <org type="institution" xml:id="struct-519855" status="VALID">
          <orgName>Xuzhou Medical University</orgName>
          <desc>
            <address>
              <country key="CN"/>
            </address>
            <ref type="url">http://en.xzhmu.edu.cn/</ref>
          </desc>
        </org>
        <org type="laboratory" xml:id="struct-548220" status="VALID">
          <orgName>Institut de Química Computacional i Catàlisi</orgName>
          <orgName type="acronym">IQCC</orgName>
          <desc>
            <address>
              <addrLine>Campus Montilivi, 17003 Girona, Catalonia</addrLine>
              <country key="ES"/>
            </address>
            <ref type="url">http://iqcc.udg.edu/wordpress/</ref>
          </desc>
          <listRelation>
            <relation active="#struct-364151" type="direct"/>
          </listRelation>
        </org>
        <org type="laboratory" xml:id="struct-194938" status="VALID">
          <idno type="IdRef">161775241</idno>
          <idno type="ISNI">0000 0004 0385 6584</idno>
          <idno type="RNSR">200612270R</idno>
          <idno type="ROR">https://ror.org/00adwkx90</idno>
          <idno type="Wikidata">Q30261343</idno>
          <orgName>Institut des Sciences Chimiques de Rennes</orgName>
          <orgName type="acronym">ISCR</orgName>
          <date type="start">2006-01-01</date>
          <desc>
            <address>
              <addrLine>Campus de Beaulieu - Bât. 10 Avenue du Général Leclerc 35042 Rennes Cedex</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">https://iscr.univ-rennes.fr/</ref>
          </desc>
          <listRelation>
            <relation active="#struct-105160" type="direct"/>
            <relation active="#struct-117606" type="direct"/>
            <relation active="#struct-301232" type="indirect"/>
            <relation active="#struct-300373" type="direct"/>
            <relation active="#struct-341038" type="direct"/>
            <relation name="UMR6226" active="#struct-441569" type="direct"/>
          </listRelation>
        </org>
        <org type="institution" xml:id="struct-364151" status="VALID">
          <idno type="ISNI">0000 0001 2179 7512</idno>
          <idno type="ROR">https://ror.org/01xdxns91</idno>
          <orgName>Universitat de Girona = University of Girona</orgName>
          <orgName type="acronym">UdG</orgName>
          <date type="start">1991-01-01</date>
          <desc>
            <address>
              <addrLine>Plaça Sant Domènec, 3 - Edifici Les Àligues - 17004 Girona</addrLine>
              <country key="ES"/>
            </address>
            <ref type="url">http://www2.udg.edu/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-105160" status="VALID">
          <idno type="IdRef">26693823X</idno>
          <idno type="ROR">https://ror.org/015m7wh34</idno>
          <orgName>Université de Rennes</orgName>
          <orgName type="acronym">UR</orgName>
          <desc>
            <address>
              <addrLine>Campus de Beaulieu, 263 avenue Général Leclerc, CS 74205, 35042 RENNES CEDEX</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">https://www.univ-rennes.fr/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-117606" status="VALID">
          <idno type="ROR">https://ror.org/04xaa4j22</idno>
          <orgName>Institut National des Sciences Appliquées - Rennes</orgName>
          <orgName type="acronym">INSA Rennes</orgName>
          <desc>
            <address>
              <addrLine>20, avenue des Buttes de Coësmes - CS 70839 - 35708 Rennes cedex 7</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.insa-rennes.fr/</ref>
          </desc>
          <listRelation>
            <relation active="#struct-301232" type="direct"/>
          </listRelation>
        </org>
        <org type="regroupinstitution" xml:id="struct-301232" status="VALID">
          <idno type="IdRef">162105150</idno>
          <orgName>Institut National des Sciences Appliquées</orgName>
          <orgName type="acronym">INSA</orgName>
          <desc>
            <address>
              <country key="FR"/>
            </address>
          </desc>
        </org>
        <org type="institution" xml:id="struct-300373" status="VALID">
          <idno type="ROR">https://ror.org/01h0ffh48</idno>
          <orgName>Ecole Nationale Supérieure de Chimie de Rennes</orgName>
          <orgName type="acronym">ENSCR</orgName>
          <desc>
            <address>
              <country key="FR"/>
            </address>
          </desc>
        </org>
        <org type="institution" xml:id="struct-341038" status="VALID">
          <idno type="IdRef">232435103</idno>
          <idno type="ISNI">000000010626358X</idno>
          <idno type="ROR">https://ror.org/02cte4b68</idno>
          <orgName>Institut de Chimie - CNRS Chimie</orgName>
          <orgName type="acronym">INC-CNRS</orgName>
          <date type="start">2009-10-01</date>
          <desc>
            <address>
              <addrLine>CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE3 rue Michel-Ange75794 PARIS CEDEX 16 - France</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.cnrs.fr/inc</ref>
          </desc>
        </org>
        <org type="regroupinstitution" xml:id="struct-441569" status="VALID">
          <idno type="IdRef">02636817X</idno>
          <idno type="ISNI">0000000122597504</idno>
          <idno type="ROR">https://ror.org/02feahw73</idno>
          <orgName>Centre National de la Recherche Scientifique</orgName>
          <orgName type="acronym">CNRS</orgName>
          <date type="start">1939-10-19</date>
          <desc>
            <address>
              <country key="FR"/>
            </address>
            <ref type="url">https://www.cnrs.fr/</ref>
          </desc>
        </org>
      </listOrg>
      <listOrg type="projects">
        <org type="anrProject" xml:id="projanr-54116" status="VALID">
          <idno type="anr">ANR-19-CE07-0039</idno>
          <orgName>REMOTCAT</orgName>
          <desc>Fonctionalisation "remote" des molecules par catalyse supramoleculaire</desc>
          <date type="start">2019</date>
        </org>
      </listOrg>
    </back>
  </text>
</TEI>