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dc.contributor.author | Takeda, Youhei | en |
dc.contributor.author | Kuroda, Akinobu | en |
dc.contributor.author | Sameera, W. M C | en |
dc.contributor.author | Morokuma, Keiji | en |
dc.contributor.author | Minakata, Satoshi | en |
dc.contributor.alternative | 諸熊, 奎治 | ja |
dc.date.accessioned | 2016-10-14T05:28:32Z | - |
dc.date.available | 2016-10-14T05:28:32Z | - |
dc.date.issued | 2016-06-09 | - |
dc.identifier.issn | 2041-6539 | - |
dc.identifier.uri | http://hdl.handle.net/2433/216975 | - |
dc.description.abstract | A palladium catalyzed regioselective borylative ring opening reaction of 2-arylaziridines to give β-amino-β-arylethylborates was developed. The reaction reported herein represents the first example of ring-opening borylation of non-vinylic aziridines and direct borylative C(sp3)-N bond cleavage of neutral organic substrates. NMR studies and density functional theory (DFT) calculations suggested that the active intermediate for the reaction is a PdL2 complex [L = P(t-Bu)2Me]. The multi-component artificial force-induced reaction method (MC-AFIR) located the transition states for the regioselectivity-determining aziridine ring opening that proceeds in an SN2 fashion, and explained the selectivity of the reaction. The full catalytic cycle consists of a selectivity-determining aziridine ring opening (oxidative addition), a proton transfer, phosphine ligand dissociation from the catalyst, boron-boron bond cleavage, and reductive elimination. Water is important to the drive the transmetalation step. The calculated overall mechanism and selectivity are consistent with the experimental results. | en |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry (RSC) | en |
dc.rights | © 2016 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. | en |
dc.title | Palladium-catalyzed regioselective and stereo-invertive ring-opening borylation of 2-arylaziridines with bis(pinacolato)diboron: Experimental and computational studies | en |
dc.type | journal article | - |
dc.type.niitype | Journal Article | - |
dc.identifier.ncid | AA12555653 | - |
dc.identifier.jtitle | Chemical Science | en |
dc.identifier.volume | 7 | - |
dc.identifier.spage | 6141 | - |
dc.identifier.epage | 6152 | - |
dc.relation.doi | 10.1039/c6sc01120a | - |
dc.textversion | publisher | - |
dc.identifier.pmid | 30034753 | - |
dcterms.accessRights | open access | - |
dc.identifier.pissn | 2041-6520 | - |
dc.identifier.eissn | 2041-6539 | - |
出現コレクション: | 学術雑誌掲載論文等 |
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