Carboxylate-Catalyzed C-Silylation of Terminal Alkynes
| dc.contributor.author | Bannykh, Anton | |
| dc.contributor.author | Pihko, Petri M. | |
| dc.date.accessioned | 2024-03-14T12:31:15Z | |
| dc.date.available | 2024-03-14T12:31:15Z | |
| dc.date.issued | 2024 | |
| dc.identifier.citation | Bannykh, A., & Pihko, P. M. (2024). Carboxylate-Catalyzed C-Silylation of Terminal Alkynes. <i>Organic Letters</i>, <i>26</i>(10), 1991-1995. <a href="https://doi.org/10.1021/acs.orglett.3c04213" target="_blank">https://doi.org/10.1021/acs.orglett.3c04213</a> | |
| dc.identifier.other | CONVID_207544075 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/93904 | |
| dc.description.abstract | A carboxylate-catalyzed, metal-free C-silylation protocol for terminal alkynes is reported using a quaternary ammonium pivalate as the catalyst and commercially available N,O-bis(silyl)acetamides as silylating agents. The reaction proceeds under mild conditions, tolerates a range of functionalities, and enables concomitant O- or N-silylation of acidic OH or NH groups. A Hammett ρ value of +1.4 ± 0.1 obtained for para-substituted 2-arylalkynes is consistent with the proposed catalytic cycle involving a turnover-determining deprotonation step. | en |
| dc.format.mimetype | application/pdf | |
| dc.language.iso | eng | |
| dc.publisher | American Chemical Society (ACS) | |
| dc.relation.ispartofseries | Organic Letters | |
| dc.rights | CC BY 4.0 | |
| dc.subject.other | Aldol reactions | |
| dc.subject.other | catalysts | |
| dc.subject.other | deprotonation | |
| dc.subject.other | hydrocarbons | |
| dc.subject.other | silylation | |
| dc.title | Carboxylate-Catalyzed C-Silylation of Terminal Alkynes | |
| dc.type | article | |
| dc.identifier.urn | URN:NBN:fi:jyu-202403142418 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.contributor.oppiaine | Nanoscience Center | fi |
| dc.contributor.oppiaine | Orgaaninen kemia | fi |
| dc.contributor.oppiaine | Nanoscience Center | en |
| dc.contributor.oppiaine | Organic 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 | 1991-1995 | |
| dc.relation.issn | 1523-7060 | |
| dc.relation.numberinseries | 10 | |
| dc.relation.volume | 26 | |
| dc.type.version | publishedVersion | |
| dc.rights.copyright | © 2024 the Authors | |
| dc.rights.accesslevel | openAccess | fi |
| dc.relation.grantnumber | 322899 | |
| dc.relation.grantnumber | 339892 | |
| dc.subject.yso | hiilivedyt | |
| dc.subject.yso | katalyytit | |
| dc.subject.yso | organometalliyhdisteet | |
| dc.format.content | fulltext | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p1169 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p15480 | |
| jyx.subject.uri | http://www.yso.fi/onto/yso/p28123 | |
| dc.rights.url | https://creativecommons.org/licenses/by/4.0/ | |
| dc.relation.doi | 10.1021/acs.orglett.3c04213 | |
| dc.relation.funder | Research Council of Finland | en |
| dc.relation.funder | Research Council of Finland | en |
| dc.relation.funder | Suomen Akatemia | fi |
| dc.relation.funder | Suomen Akatemia | fi |
| jyx.fundingprogram | Academy Project, AoF | en |
| jyx.fundingprogram | Academy Project, AoF | en |
| jyx.fundingprogram | Akatemiahanke, SA | fi |
| jyx.fundingprogram | Akatemiahanke, SA | fi |
| jyx.fundinginformation | We acknowledge financial support from the Department of Chemistry, University of Jyväskylä (JYU), and the Academy of Finland (Projects 322899 and 339892). | |
| dc.type.okm | A1 |
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