An on‐surface Diels–Alder reaction
The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on‐surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne to demonstrate an on‐surface hexadehydro‐Diels...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2021-12, Vol.60 (50), p.26346-26350 |
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| creator | Castro‐Esteban, Jesús Albrecht, Florian Fatayer, Shadi Pérez, Dolores Gross, Leo Peña, Diego |
| description | The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on‐surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne to demonstrate an on‐surface hexadehydro‐Diels–Alder reaction in a single molecule. The reaction was studied in detail by means of atomic force microscopy (AFM) with CO‐functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on‐surface synthesis, introducing the concept of atom economy in the field.
A hexadehydro‐Diels–Alder reaction was demonstrated on‐surface in single molecules of a cyclic strained triyne. The starting material, several intermediates and the product were visualized by means of atomic force microscopy (AFM) with CO‐functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on‐surface synthesis, introducing the concept of atom economy in the field. |
| doi_str_mv | 10.1002/anie.202110311 |
| format | Article |
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A hexadehydro‐Diels–Alder reaction was demonstrated on‐surface in single molecules of a cyclic strained triyne. The starting material, several intermediates and the product were visualized by means of atomic force microscopy (AFM) with CO‐functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on‐surface synthesis, introducing the concept of atom economy in the field.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>ISSN: 1521-3773</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202110311</identifier><identifier>PMID: 34664770</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Atom economy ; Atomic force microscopy ; bond-resolved AFM ; Chemical synthesis ; Communication ; Communications ; Cycloaddition ; Diels-Alder reactions ; Diels–Alder reaction ; on-surface synthesis ; Organic chemistry ; polycyclic aromatic hydrocarbons</subject><ispartof>Angewandte Chemie International Edition, 2021-12, Vol.60 (50), p.26346-26350</ispartof><rights>2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH</rights><rights>2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.</rights><rights>2021. This article is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4681-4b8223447a0a947b2d8c5159db5af5dd48110fb4adaa09398f2f1e160f11b38b3</citedby><cites>FETCH-LOGICAL-c4681-4b8223447a0a947b2d8c5159db5af5dd48110fb4adaa09398f2f1e160f11b38b3</cites><orcidid>0000-0003-3814-589X ; 0000-0002-7418-9155 ; 0000-0003-0877-5938 ; 0000-0003-4260-3208 ; 0000-0003-0100-943X ; 0000-0002-5337-4159</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202110311$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202110311$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34664770$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Castro‐Esteban, Jesús</creatorcontrib><creatorcontrib>Albrecht, Florian</creatorcontrib><creatorcontrib>Fatayer, Shadi</creatorcontrib><creatorcontrib>Pérez, Dolores</creatorcontrib><creatorcontrib>Gross, Leo</creatorcontrib><creatorcontrib>Peña, Diego</creatorcontrib><title>An on‐surface Diels–Alder reaction</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on‐surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne to demonstrate an on‐surface hexadehydro‐Diels–Alder reaction in a single molecule. The reaction was studied in detail by means of atomic force microscopy (AFM) with CO‐functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on‐surface synthesis, introducing the concept of atom economy in the field.
A hexadehydro‐Diels–Alder reaction was demonstrated on‐surface in single molecules of a cyclic strained triyne. The starting material, several intermediates and the product were visualized by means of atomic force microscopy (AFM) with CO‐functionalized tips. 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A hexadehydro‐Diels–Alder reaction was demonstrated on‐surface in single molecules of a cyclic strained triyne. The starting material, several intermediates and the product were visualized by means of atomic force microscopy (AFM) with CO‐functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on‐surface synthesis, introducing the concept of atom economy in the field.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>34664770</pmid><doi>10.1002/anie.202110311</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-3814-589X</orcidid><orcidid>https://orcid.org/0000-0002-7418-9155</orcidid><orcidid>https://orcid.org/0000-0003-0877-5938</orcidid><orcidid>https://orcid.org/0000-0003-4260-3208</orcidid><orcidid>https://orcid.org/0000-0003-0100-943X</orcidid><orcidid>https://orcid.org/0000-0002-5337-4159</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Atom economy Atomic force microscopy bond-resolved AFM Chemical synthesis Communication Communications Cycloaddition Diels-Alder reactions Diels–Alder reaction on-surface synthesis Organic chemistry polycyclic aromatic hydrocarbons |
| title | An on‐surface Diels–Alder reaction |
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