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dc.contributor.authorGuo, Lin
dc.contributor.authorSrimontree, Watchara
dc.contributor.authorZhu, Chen
dc.contributor.authorMaity, Bholanath
dc.contributor.authorLiu, Xiangqian
dc.contributor.authorCavallo, Luigi
dc.contributor.authorRueping, Magnus
dc.date.accessioned2019-05-13T11:34:24Z
dc.date.available2019-05-13T11:34:24Z
dc.date.issued2019-04-29
dc.identifier.citationGuo L, Srimontree W, Zhu C, Maity B, Liu X, et al. (2019) Nickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes. Nature Communications 10. Available: http://dx.doi.org/10.1038/s41467-019-09766-x.
dc.identifier.issn2041-1723
dc.identifier.doi10.1038/s41467-019-09766-x
dc.identifier.urihttp://hdl.handle.net/10754/652835
dc.description.abstractTransition-metal-catalyzed cross-couplings have been extensively used in the pharmaceutical and agrochemical industries for the construction of diverse C-C bonds. Conventional cross-coupling reactions require reactive electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly and not naturally abundant. Another disadvantage associated with these transformations is the need for an exogenous base to facilitate the key transmetalation step, and this reagent inevitably induces side reactions and limits the substrate scope. Here, we report an unconventional Suzuki-type approach to the synthesis of biaryls, through nickel-catalyzed deformylative cross coupling of aldehydes with organoboron reagents under base-free conditions. The transformation tolerates structurally diverse (hetero)aryl substituents on both coupling partners and shows high reactivity and excellent functional group tolerance. Furthermore, the protocol was carried out on gram scale and successfully applied to the functionalization of complex biologically active molecules. Mechanistic investigations support a catalytic cycle involving the oxidative addition of the nickel into the aldehyde C(acyl)-H bond with subsequent hydride transfer, transmetalation, decarbonylation and reductive elimination processes.
dc.description.sponsorshipL.G. acknowledges the support from the China Scholarship Council. C.Z., B.M., L.C., and M.R. acknowledge King Abdullah University of Science and Technology (KAUST) for support and the KAUST Supercomputing Laboratory for providing the computational resources of the supercomputer Shaheen II. This research was supported by King Abdullah University of Science and Technology (KAUST) Office of Sponsored Research under award number URF/1/3030-01.
dc.publisherSpringer Nature
dc.relation.urlhttps://www.nature.com/articles/s41467-019-09766-x
dc.rightsThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
dc.titleNickel-catalyzed Suzuki–Miyaura cross-couplings of aldehydes
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalNature Communications
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
kaust.personMaity, Bholanath
kaust.personCavallo, Luigi
kaust.grant.numberURF/1/3030-01
refterms.dateFOA2019-05-14T06:45:14Z
dc.date.published-online2019-04-29
dc.date.published-print2019-12


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