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Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides
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dc.contributor.author | Buchanan, Helena S. | |
dc.contributor.author | Pauff, Steven M. | |
dc.contributor.author | Kosmidis, Tilemachos D. | |
dc.contributor.author | Taladriz-Sender, Andrea | |
dc.contributor.author | Rutherford, Olivia I. | |
dc.contributor.author | Hatit, Marine Z. C. | |
dc.contributor.author | Fenner, Sabine | |
dc.contributor.author | Watson, Allan J. B. | |
dc.contributor.author | Burley, Glenn A. | |
dc.date.accessioned | 2018-02-06T15:30:33Z | |
dc.date.available | 2018-02-06T15:30:33Z | |
dc.date.issued | 2017-07-21 | |
dc.identifier | 252194070 | |
dc.identifier | 5e20c732-f256-43ce-acc7-ff547c842c07 | |
dc.identifier | 85025166806 | |
dc.identifier.citation | Buchanan , H S , Pauff , S M , Kosmidis , T D , Taladriz-Sender , A , Rutherford , O I , Hatit , M Z C , Fenner , S , Watson , A J B & Burley , G A 2017 , ' Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides ' , Organic Letters , vol. 19 , no. 14 , pp. 3759-3762 . https://doi.org/10.1021/acs.orglett.7b01602 | en |
dc.identifier.issn | 1523-7060 | |
dc.identifier.other | RIS: urn:D71D645F98CB90E11C2D33114717DA2D | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/56639172 | |
dc.identifier.uri | https://hdl.handle.net/10023/12680 | |
dc.description | This work was supported by an EPSRC-GSK industrial CASE studentship for H.B., a University studentship for T.D.K., and postdoctoral funding for S.P. by the Leverhulme Trust (RPG-2014-313). | en |
dc.description.abstract | Two Pd-catalyzed methods to access 6-heteroaryl 2-aminopurine ribonucleosides from 6-chloroguanosine are described. First, Pd-132-catalyzed Suzuki–Miyaura cross-coupling using a series of boron substrates and 6-chloroguanosine forms 6-heteroaryl-2-aminopurines in a single step. The versatility of 6-chloroguanosine is further demonstrated using a modified Sonogashira coupling employing potassium iodide as an additive. Finally, the utility of the 6-alkynyl-2-aminopurine ribonucleoside as a dipolarophile in [3 + 2] cycloadditions is presented, affording triazoles and isoxazoles when reacted with azide and isonitrile 1,3-dipoles, respectively. | |
dc.format.extent | 4 | |
dc.format.extent | 1065794 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Letters | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Modular,step-efficient palladium-catalyzed cross-coupling strategy to access C6-heteroaryl 2-aminopurine ribonucleosides | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1021/acs.orglett.7b01602 | |
dc.description.status | Peer reviewed | en |
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