From propargylic amides to functionalized oxazoles: Domino gold catalysis/oxidation by dioxygen
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroper...
Gespeichert in:
| Hauptverfasser: | , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
July 17, 2012
|
| In: |
The journal of organic chemistry
Year: 2012, Jahrgang: 77, Heft: 15, Pages: 6394-6408 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/jo301288w |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1021/jo301288w Verlag, Volltext: http://pubs.acs.org/doi/10.1021/jo301288w 
|
| Verfasserangaben: | A. Stephen K. Hashmi, Maria Camila Blanco Jaimes, Andreas M. Schuster, and Frank Rominger |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1580750869 | ||
| 003 | DE-627 | ||
| 005 | 20220815003110.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 180906s2012 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/jo301288w |2 doi | |
| 035 | |a (DE-627)1580750869 | ||
| 035 | |a (DE-576)510750869 | ||
| 035 | |a (DE-599)BSZ510750869 | ||
| 035 | |a (OCoLC)1341018251 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 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 From propargylic amides to functionalized oxazoles |b Domino gold catalysis/oxidation by dioxygen |c A. Stephen K. Hashmi, Maria Camila Blanco Jaimes, Andreas M. Schuster, and Frank Rominger |
| 264 | 1 | |c July 17, 2012 | |
| 300 | |a 15 | ||
| 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 06.09.2018 | ||
| 520 | |a A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride. | ||
| 700 | 1 | |a Blanco Jaimes, Maria Camila |d 1985- |e VerfasserIn |0 (DE-588)1058987224 |0 (DE-627)797899332 |0 (DE-576)415058937 |4 aut | |
| 700 | 1 | |a Schuster, Andreas M. |e VerfasserIn |0 (DE-588)1247756769 |0 (DE-627)1782357610 |4 aut | |
| 700 | 1 | |a Rominger, Frank |d 1964- |e VerfasserIn |0 (DE-588)1019978228 |0 (DE-627)691067821 |0 (DE-576)359202756 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t The journal of organic chemistry |d [Erscheinungsort nicht ermittelbar] : American Chemical Society, 1936 |g 77(2012), 15, Seite 6394-6408 |h Online-Ressource |w (DE-627)268133387 |w (DE-600)1472273-2 |w (DE-576)090854292 |x 1520-6904 |7 nnas |a From propargylic amides to functionalized oxazoles Domino gold catalysis/oxidation by dioxygen |
| 773 | 1 | 8 | |g volume:77 |g year:2012 |g number:15 |g pages:6394-6408 |g extent:15 |a From propargylic amides to functionalized oxazoles Domino gold catalysis/oxidation by dioxygen |
| 776 | 0 | 8 | |i Erscheint auch als |n Druck-Ausgabe |t From propargylic amides to functionalized oxazoles |d 2012 |w (DE-627)1439974748 |w (DE-576)369974743 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/jo301288w |x Verlag |x Resolving-System |3 Volltext |
| 856 | 4 | 0 | |u http://pubs.acs.org/doi/10.1021/jo301288w |x Verlag |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20180906 | ||
| 993 | |a Article | ||
| 998 | |g 1019978228 |a Rominger, Frank |m 1019978228:Rominger, Frank |d 120000 |d 120100 |e 120000PR1019978228 |e 120100PR1019978228 |k 0/120000/ |k 1/120000/120100/ |p 4 |y j | ||
| 998 | |g 1247756769 |a Schuster, Andreas M. |m 1247756769:Schuster, Andreas M. |d 120000 |d 120100 |e 120000PS1247756769 |e 120100PS1247756769 |k 0/120000/ |k 1/120000/120100/ |p 3 | ||
| 998 | |g 1058987224 |a Blanco Jaimes, Maria Camila |m 1058987224:Blanco Jaimes, Maria Camila |d 120000 |d 120100 |e 120000PB1058987224 |e 120100PB1058987224 |k 0/120000/ |k 1/120000/120100/ |p 2 | ||
| 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 | ||
| 999 | |a KXP-PPN1580750869 |e 3024852700 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"recId":"1580750869","name":{"displayForm":["A. Stephen K. Hashmi, Maria Camila Blanco Jaimes, Andreas M. Schuster, and Frank Rominger"]},"origin":[{"dateIssuedKey":"2012","dateIssuedDisp":"July 17, 2012"}],"person":[{"given":"A. Stephen K.","display":"Hashmi, A. Stephen K.","family":"Hashmi","role":"aut"},{"family":"Blanco Jaimes","display":"Blanco Jaimes, Maria Camila","given":"Maria Camila","role":"aut"},{"display":"Schuster, Andreas M.","given":"Andreas M.","family":"Schuster","role":"aut"},{"role":"aut","given":"Frank","display":"Rominger, Frank","family":"Rominger"}],"language":["eng"],"title":[{"subtitle":"Domino gold catalysis/oxidation by dioxygen","title_sort":"From propargylic amides to functionalized oxazoles","title":"From propargylic amides to functionalized oxazoles"}],"type":{"bibl":"article-journal","media":"Online-Ressource"},"id":{"eki":["1580750869"],"doi":["10.1021/jo301288w"]},"physDesc":[{"extent":"15 S."}],"relHost":[{"note":["Gesehen am 25.08.2020"],"physDesc":[{"extent":"Online-Ressource"}],"part":{"year":"2012","pages":"6394-6408","text":"77(2012), 15, Seite 6394-6408","volume":"77","extent":"15","issue":"15"},"id":{"issn":["1520-6904"],"zdb":["1472273-2"],"eki":["268133387"]},"title":[{"subtitle":"web edition","title_sort":"journal of organic chemistry","title":"The journal of organic chemistry"}],"corporate":[{"role":"isb","display":"American Chemical Society"}],"origin":[{"publisherPlace":"[Erscheinungsort nicht ermittelbar]","dateIssuedKey":"1936","dateIssuedDisp":"1936-","publisher":"American Chemical Society"}],"type":{"media":"Online-Ressource","bibl":"periodical"},"pubHistory":["1.1936/37 -"],"language":["eng"],"disp":"From propargylic amides to functionalized oxazoles Domino gold catalysis/oxidation by dioxygenThe journal of organic chemistry","recId":"268133387"}],"note":["Gesehen am 06.09.2018"]} | ||
| SRT | |a HASHMIASTEFROMPROPAR1720 | ||