Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/148223
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dc.contributor.authorRen, Shi-Caoen_US
dc.contributor.authorLv, Wen-Xinen_US
dc.contributor.authorYang, Xingen_US
dc.contributor.authorYan, Jia-Leien_US
dc.contributor.authorXu, Junen_US
dc.contributor.authorWang, Fang-Xinen_US
dc.contributor.authorHao, Linen_US
dc.contributor.authorChai, Huifangen_US
dc.contributor.authorJin, Zhichaoen_US
dc.contributor.authorChi, Robin Yongguien_US
dc.date.accessioned2021-04-26T01:01:46Z-
dc.date.available2021-04-26T01:01:46Z-
dc.date.issued2021-
dc.identifier.citationRen, S., Lv, W., Yang, X., Yan, J., Xu, J., Wang, F., Hao, L., Chai, H., Jin, Z. & Chi, R. Y. (2021). Carbene-catalyzed alkylation of carboxylic esters via direct photoexcitation of acyl azolium intermediates. ACS Catalysis, 11(5), 2925-2934. https://dx.doi.org/10.1021/acscatal.1c00165en_US
dc.identifier.issn2155-5435en_US
dc.identifier.other0000-0003-4156-2061-
dc.identifier.other0000-0001-9221-5751-
dc.identifier.other0000-0003-3003-6437-
dc.identifier.other0000-0003-0573-257X-
dc.identifier.urihttps://hdl.handle.net/10356/148223-
dc.description.abstractA carbene-catalyzed reductive coupling reaction of carboxylic esters and substituted Hantzsch esters is disclosed. Key steps of this reaction include one-electron reduction of a carbene catalyst-bound acyl azolium intermediate to generate the corresponding radical intermediate for subsequent alkylation reactions. The reaction is promoted by irradiation with visible light without the involvement of transition-metal photocatalysts. Mechanistic studies suggest that direct photoexcitation of the in situ formed acyl azolium intermediate is likely responsible for this light-induced one-electron-reduction process. Photoexcitation converts the acyl azolium intermediate to a single-electron oxidant, enabling single-electron oxidation of Hantzsch esters to generate radical intermediates. Our reactions work well for a broad range of aryl carboxylic ester and Hantzsch ester substrates. Sophisticated structures, including those present in medicines, can be incorporated into ketone molecules using our approach via very mild conditions that tolerate various functional groups.en_US
dc.description.sponsorshipMinistry of Education (MOE)en_US
dc.description.sponsorshipNational Research Foundation (NRF)en_US
dc.language.isoenen_US
dc.relation.ispartofACS Catalysisen_US
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.1c00165en_US
dc.subjectScienceen_US
dc.titleCarbene-catalyzed alkylation of carboxylic esters via direct photoexcitation of acyl azolium intermediatesen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doi10.1021/acscatal.1c00165-
dc.description.versionAccepted versionen_US
dc.identifier.scopus2-s2.0-85102002841-
dc.identifier.issue5en_US
dc.identifier.volume11en_US
dc.identifier.spage2925en_US
dc.identifier.epage2934en_US
dc.subject.keywordsN-heterocyclic Carbeneen_US
dc.subject.keywordsAcyl Azoliumen_US
dc.description.acknowledgementThe authors acknowl- edge financial support from the Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016- 06), the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG108/16, RG5/19, and RG1/18), MOE AcRF Tier 3 Award (MOE2018-T3-1-003), the Agency for Science, Technology and Research (A*STAR) under its A*STAR AME IRG Award (A1783c0008 and A1783c0010), the GSK-EDB Trust Fund, Nanyang Research Award Grant, Nanyang Technological University, the National Natural Science Foundation of China (21772029, 21801051 21961006, 82360589, and 81360589), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802 and [2019] 1020), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], the Guizhou University of Traditional Chinese Medicine (China), and Guizhou University.en_US
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