dc.contributor.author | Hicks, Jamie | |
dc.contributor.author | Vasko, Petra | |
dc.contributor.author | Heilmann, Andreas | |
dc.contributor.author | Goicoechea, Jose | |
dc.contributor.author | Aldridge, Simon | |
dc.date.accessioned | 2020-07-30T06:10:02Z | |
dc.date.available | 2020-07-30T06:10:02Z | |
dc.date.issued | 2020 | |
dc.identifier.citation | Hicks, J., Vasko, P., Heilmann, A., Goicoechea, J., & Aldridge, S. (2020). Arene C‐H activation at aluminium(I) : meta selectivity driven by the electronics of SNAr chemistry. <i>Angewandte Chemie</i>, <i>59</i>(46), 20376-20380. <a href="https://doi.org/10.1002/anie.202008557" target="_blank">https://doi.org/10.1002/anie.202008557</a> | |
dc.identifier.other | CONVID_41659921 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/71279 | |
dc.description.abstract | The reactivity of the electron-rich anionic Al(I) (‘aluminyl’) compound K 2 [(NON)Al] 2 (NON = 4,5-bis(2,6-diisopropylanilido)-2,7-di- tert -butyl-9,9-dimethylxanthene) towards mono- and disubstituted arenes is reported. C-H activation chemistry with n -butylbenzene gives exclusively the product of activation at the arene meta position. Mechanistically, this transformation proceeds in a single step via a concerted Meisenheimer-type transition state. Selectivity is therefore based on similar electronic factors to classical S N Ar chemistry, which implies the destabilization of transition states featuring electron-donating groups in either the ortho or the para positions. In the cases of toluene and the three isomers of xylene, benzylic C-H activation is also possible, with the product(s) formed reflecting the feasibility (or otherwise) of competing arene C-H activation at a site which is neither ortho or para to a methyl substituent. | en |
dc.format.mimetype | application/pdf | |
dc.language | eng | |
dc.language.iso | eng | |
dc.publisher | Wiley | |
dc.relation.ispartofseries | Angewandte Chemie | |
dc.rights | CC BY-NC 4.0 | |
dc.subject.other | aluminium | |
dc.subject.other | aluminyl nucleophile | |
dc.subject.other | C-H activation | |
dc.subject.other | arenes | |
dc.subject.other | SNAr mechanism | |
dc.title | Arene C‐H activation at aluminium(I) : meta selectivity driven by the electronics of SNAr chemistry | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-202007305427 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
dc.contributor.oppiaine | Inorganic and Analytical Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.format.pagerange | 20376-20380 | |
dc.relation.issn | 1433-7851 | |
dc.relation.numberinseries | 46 | |
dc.relation.volume | 59 | |
dc.type.version | acceptedVersion | |
dc.rights.copyright | 2020 The Authors. | |
dc.rights.accesslevel | openAccess | fi |
dc.relation.grantnumber | 314794 | |
dc.subject.yso | alumiini | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p19563 | |
dc.rights.url | https://creativecommons.org/licenses/by-nc/4.0/ | |
dc.relation.doi | 10.1002/anie.202008557 | |
dc.relation.funder | Research Council of Finland | en |
dc.relation.funder | Suomen Akatemia | fi |
jyx.fundingprogram | Postdoctoral Researcher, AoF | en |
jyx.fundingprogram | Tutkijatohtori, SA | fi |
jyx.fundinginformation | We thank the Leverhulme Trust (RP-2018-246) for funding aspects of this work. PV thanks the Academy of Finland (Grant No. 314794) and Prof Heikki Tuononen for providing computational resources | |
dc.type.okm | A1 | |