Gold-catalyzed synthesis of N,O-heterocycles
The selective synthesis of oxazoles, alkylidene oxazoles, and 1,3-oxazines from N -propargyl carboxamides by choosing gold(III) or gold(I) catalysts and selecting terminal or internal alkynes as substrates is discussed. The mechanistic studies based on labeling experiments and intensive in situ NMR...
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Deutsch |
| Veröffentlicht: |
18. Februar 2010
|
| In: |
Pure and applied chemistry
Year: 2010, Jahrgang: 82, Heft: 3, Pages: 657-668 |
| ISSN: | 1365-3075 |
| DOI: | 10.1351/PAC-CON-09-10-17 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1351/PAC-CON-09-10-17 Verlag, lizenzpflichtig, Volltext: https://www.degruyterbrill.com/document/doi/10.1351/PAC-CON-09-10-17/html 
|
| Verfasserangaben: | A. Stephen K. Hashmi (Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg) |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1840021780 | ||
| 003 | DE-627 | ||
| 005 | 20250529235117.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 230324s2010 xx |||||o 00| ||ger c | ||
| 024 | 7 | |a 10.1351/PAC-CON-09-10-17 |2 doi | |
| 035 | |a (DE-627)1840021780 | ||
| 035 | |a (DE-599)KXP1840021780 | ||
| 035 | |a (OCoLC)1389807046 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a ger | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Hashmi, A. Stephen K. |d 1963- |e VerfasserIn |0 (DE-588)101199576X |0 (DE-627)704823926 |0 (DE-576)169176665 |4 aut | |
| 245 | 1 | 0 | |a Gold-catalyzed synthesis of N,O-heterocycles |c A. Stephen K. Hashmi (Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg) |
| 264 | 1 | |c 18. Februar 2010 | |
| 300 | |b Diagramme | ||
| 300 | |a 12 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 24.03.2023 | ||
| 520 | |a The selective synthesis of oxazoles, alkylidene oxazoles, and 1,3-oxazines from N -propargyl carboxamides by choosing gold(III) or gold(I) catalysts and selecting terminal or internal alkynes as substrates is discussed. The mechanistic studies based on labeling experiments and intensive in situ NMR studies indicate an anti -oxyauration step and a proto-deauration with retention of the sterical arrangement at the double bond. The synthetic scope for gold(I) catalysts is very broad, allowing selective conversions to products with properties of chelate ligands, reactions of bromoarenes and the formation of acceptor-substituted oxazoles. With N -heterocyclic carbene (NHC) ligands in the presence of a base, even the vinylgold intermediates of the reactions leading to 1,3-oxazines could be isolated, a reaction with a great potential for future mechanistic studies and future applications of gold catalysis. | ||
| 650 | 4 | |a alkynes | |
| 650 | 4 | |a amides | |
| 650 | 4 | |a gold | |
| 650 | 4 | |a oxazoles | |
| 650 | 4 | |a transition-metal-catalyzed reactions | |
| 773 | 0 | 8 | |i Enthalten in |t Pure and applied chemistry |d Berlin : de Gruyter, 1960 |g 82(2010), 3 vom: Feb., Seite 657-668 |h Online-Ressource |w (DE-627)320616746 |w (DE-600)2022101-0 |w (DE-576)091170389 |x 1365-3075 |7 nnas |a Gold-catalyzed synthesis of N,O-heterocycles |
| 773 | 1 | 8 | |g volume:82 |g year:2010 |g number:3 |g month:02 |g pages:657-668 |g extent:12 |a Gold-catalyzed synthesis of N,O-heterocycles |
| 776 | 0 | 8 | |i Erscheint auch als |n Druck-Ausgabe |a Hashmi, A. Stephen K., 1963 - |t Gold-catalyzed synthesis of N,O-heterocycles |d 2010 |w (DE-627)1630531464 |w (DE-576)375448012 |
| 856 | 4 | 0 | |u https://doi.org/10.1351/PAC-CON-09-10-17 |x Verlag |x Resolving-System |z lizenzpflichtig |3 Volltext |
| 856 | 4 | 0 | |u https://www.degruyterbrill.com/document/doi/10.1351/PAC-CON-09-10-17/html |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20230324 | ||
| 993 | |a Article | ||
| 994 | |a 2010 | ||
| 998 | |g 101199576X |a Hashmi, A. Stephen K. |m 101199576X:Hashmi, A. Stephen K. |d 120000 |d 120100 |e 120000PH101199576X |e 120100PH101199576X |k 0/120000/ |k 1/120000/120100/ |p 1 |x j |y j | ||
| 999 | |a KXP-PPN1840021780 |e 4296702173 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"note":["Gesehen am 24.03.2023"],"type":{"bibl":"article-journal","media":"Online-Ressource"},"origin":[{"dateIssuedKey":"2010","dateIssuedDisp":"18. Februar 2010"}],"title":[{"title":"Gold-catalyzed synthesis of N,O-heterocycles","title_sort":"Gold-catalyzed synthesis of N,O-heterocycles"}],"person":[{"role":"aut","family":"Hashmi","given":"A. Stephen K.","display":"Hashmi, A. Stephen K."}],"language":["ger"],"physDesc":[{"noteIll":"Diagramme","extent":"12 S."}],"relHost":[{"name":{"displayForm":["IUPAC"]},"recId":"320616746","id":{"issn":["1365-3075"],"zdb":["2022101-0"],"eki":["320616746"]},"language":["eng"],"corporate":[{"display":"International Union of Pure and Applied Chemistry","role":"isb"}],"part":{"pages":"657-668","volume":"82","extent":"12","issue":"3","year":"2010","text":"82(2010), 3 vom: Feb., Seite 657-668"},"physDesc":[{"extent":"Online-Ressource"}],"disp":"Gold-catalyzed synthesis of N,O-heterocyclesPure and applied chemistry","type":{"bibl":"periodical","media":"Online-Ressource"},"origin":[{"dateIssuedKey":"1960","publisherPlace":"Berlin ; Oxford ; Research Triangle Park, NC","dateIssuedDisp":"1960-","publisher":"de Gruyter ; Blackwell Science ; IUPAC Science"}],"pubHistory":["1.1960 -"],"title":[{"title":"Pure and applied chemistry","title_sort":"Pure and applied chemistry"}],"note":["Gesehen am 19. April 2016"]}],"name":{"displayForm":["A. Stephen K. Hashmi (Institute of Organic Chemistry, Ruprecht-Karls-University Heidelberg)"]},"id":{"eki":["1840021780"],"doi":["10.1351/PAC-CON-09-10-17"]},"recId":"1840021780"} | ||
| SRT | |a HASHMIASTEGOLDCATALY1820 | ||