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dc.contributor.authorBonciolini, Stefano
dc.contributor.authorPulcinella, Antonio
dc.contributor.authorLeone, Matteo
dc.contributor.authorSchiroli, Deborah
dc.contributor.authorRuiz, Adrian Luguera
dc.contributor.authorSorato, Andrea
dc.contributor.authorDubois, Maryne A.J.
dc.contributor.authorGopalakrishnan, Ranganath
dc.contributor.authorMasson, Geraldine
dc.contributor.authorCa', Nicola Della
dc.contributor.authorProtti, Stefano
dc.contributor.authorFagnoni, Maurizio
dc.contributor.authorZysman-Colman, Eli
dc.contributor.authorJohansson, Magnus
dc.contributor.authorNoël, Timothy
dc.date.accessioned2024-02-27T16:30:08Z
dc.date.available2024-02-27T16:30:08Z
dc.date.issued2024-02-19
dc.identifier299423830
dc.identifiere1a34eb6-481c-4960-a061-a58bb498870e
dc.identifier85185477742
dc.identifier.citationBonciolini , S , Pulcinella , A , Leone , M , Schiroli , D , Ruiz , A L , Sorato , A , Dubois , M A J , Gopalakrishnan , R , Masson , G , Ca' , N D , Protti , S , Fagnoni , M , Zysman-Colman , E , Johansson , M & Noël , T 2024 , ' Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes ' , Nature Communications , vol. 15 , 1509 . https://doi.org/10.1038/s41467-024-45804-zen
dc.identifier.issn2041-1723
dc.identifier.otherORCID: /0000-0001-7183-6022/work/154532671
dc.identifier.urihttps://hdl.handle.net/10023/29361
dc.descriptionAuthors are grateful to have received generous funding from the European Union H2020 research and innovation program under the Marie S. Curie Grant Agreement (PhotoReAct, No 956324, S.B., M.L., A.L., G.M., E.Z.C., T.N.; CHAIR, No 860762, A.P., M.J., T.N.)en
dc.description.abstractIn contemporary drug discovery, enhancing the sp3-hybridized character of molecular structures is paramount, necessitating innovative synthetic methods. Herein, we introduce a deoxygenative cross-electrophile coupling technique that pairs easily accessible carboxylic acid-derived redox-active esters with aldehyde sulfonyl hydrazones, employing Eosin Y as an organophotocatalyst under visible light irradiation. This approach serves as a versatile, metal-free C(sp3)−C(sp3) cross-coupling platform. We demonstrate its synthetic value as a safer, broadly applicable C1 homologation of carboxylic acids, offering an alternative to the traditional Arndt-Eistert reaction. Additionally, our method provides direct access to cyclic and acyclic β-arylethylamines using diverse aldehyde-derived sulfonyl hydrazones. Notably, the methodology proves to be compatible with the late-stage functionalization of peptides on solid-phase, streamlining the modification of intricate peptides without the need for exhaustive de-novo synthesis.
dc.format.extent9
dc.format.extent1182232
dc.language.isoeng
dc.relation.ispartofNature Communicationsen
dc.subjectQD Chemistryen
dc.subjectRR-NDASen
dc.subject.lccQDen
dc.titleMetal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydesen
dc.typeJournal articleen
dc.contributor.sponsorEuropean Commissionen
dc.contributor.institutionUniversity of St Andrews. Centre for Energy Ethicsen
dc.contributor.institutionUniversity of St Andrews. Organic Semiconductor Centreen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doi10.1038/s41467-024-45804-z
dc.description.statusPeer revieweden
dc.identifier.grantnumber956324en


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