Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen
The asymmetric ruthenium-catalyzed reductive amination employing ammonia and hydrogen to primary amines is described. Here we demonstrate the capability of our catalyst to perform a chemo- and enantioselective process while using simple ammonia gas as a reagent, one of the most attractive and indust...
Gespeichert in:
| Hauptverfasser: | , , , , , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2018
|
| In: |
Journal of the American Chemical Society
Year: 2017, Jahrgang: 140, Heft: 1, Pages: 355-361 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/jacs.7b10496 |
| Online-Zugang: | Verlag, Volltext: http://dx.doi.org/10.1021/jacs.7b10496 Verlag, Volltext: https://doi.org/10.1021/jacs.7b10496 
|
| Verfasserangaben: | Joan Gallardo-Donaire, Marko Hermsen, Jedrzej Wysocki, Martin Ernst, Frank Rominger, Oliver Trapp, A. Stephen K. Hashmi, Ansgar Schäfer, Peter Comba, and Thomas Schaub |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 157631104X | ||
| 003 | DE-627 | ||
| 005 | 20220814162206.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 180613r20182017xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/jacs.7b10496 |2 doi | |
| 035 | |a (DE-627)157631104X | ||
| 035 | |a (DE-576)50631104X | ||
| 035 | |a (DE-599)BSZ50631104X | ||
| 035 | |a (OCoLC)1341011470 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Gallardo-Donaire, Joan |e VerfasserIn |0 (DE-588)1161017607 |0 (DE-627)1024429512 |0 (DE-576)506312224 |4 aut | |
| 245 | 1 | 0 | |a Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen |c Joan Gallardo-Donaire, Marko Hermsen, Jedrzej Wysocki, Martin Ernst, Frank Rominger, Oliver Trapp, A. Stephen K. Hashmi, Ansgar Schäfer, Peter Comba, and Thomas Schaub |
| 264 | 1 | |c 2018 | |
| 300 | |a 7 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Published: December 1, 2017 | ||
| 500 | |a Gesehen am 13.06.2018 | ||
| 520 | |a The asymmetric ruthenium-catalyzed reductive amination employing ammonia and hydrogen to primary amines is described. Here we demonstrate the capability of our catalyst to perform a chemo- and enantioselective process while using simple ammonia gas as a reagent, one of the most attractive and industrially relevant nitrogen sources. The presence of a catalytic amount of ammonium iodide was essential for obtaining good yields and enantioselectivities. The mechanism of this reaction was investigated by DFT and we found a viable pathway that also explains the trend and magnitude of enantioselectivity through the halide series in good agreement with the experimental data. The in-depth investigation of substrate conformers during the reaction turned out to be crucial in obtaining an accurate prediction of the enantioselectivity. Furthermore, we report the crystallographic data of the chiral [Ru(I)H(CO)((S,S)-f-binaphane)(PPh3)] complex, which we identified as the most efficient catalyst in our investigation. | ||
| 534 | |c 2017 | ||
| 700 | 1 | |a Hermsen, Marko |e VerfasserIn |0 (DE-588)1159789681 |0 (DE-627)102246356X |0 (DE-576)505299852 |4 aut | |
| 700 | 1 | |a Wysocki, Jędrzej |d 1987- |e VerfasserIn |0 (DE-588)1073900223 |0 (DE-627)829778837 |0 (DE-576)435392514 |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 | |
| 700 | 1 | |a Trapp, Oliver |d 1973- |e VerfasserIn |0 (DE-588)123258634 |0 (DE-627)70623071X |0 (DE-576)184366003 |4 aut | |
| 700 | 1 | |a Hashmi, A. Stephen K. |d 1963- |e VerfasserIn |0 (DE-588)101199576X |0 (DE-627)704823926 |0 (DE-576)169176665 |4 aut | |
| 700 | 1 | |a Comba, Peter |d 1953- |e VerfasserIn |0 (DE-588)122976843 |0 (DE-627)082271712 |0 (DE-576)160608988 |4 aut | |
| 700 | 1 | |a Schaub, Thomas |d 1980- |e VerfasserIn |0 (DE-588)132888343 |0 (DE-627)690969082 |0 (DE-576)299482499 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |a American Chemical Society |t Journal of the American Chemical Society |d Washington, DC : ACS Publications, 1879 |g 140(2018), 1, Seite 355-361 |w (DE-627)268132836 |w (DE-600)1472210-0 |w (DE-576)090854284 |x 1520-5126 |7 nnas |
| 773 | 1 | 8 | |g volume:140 |g year:2018 |g number:1 |g pages:355-361 |g extent:7 |a Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/jacs.7b10496 |x Verlag |x Resolving-System |3 Volltext |
| 856 | 4 | 0 | |u https://doi.org/10.1021/jacs.7b10496 |x Verlag |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20180613 | ||
| 993 | |a Article | ||
| 994 | |a 2018 | ||
| 998 | |g 132888343 |a Schaub, Thomas |m 132888343:Schaub, Thomas |p 10 |y j | ||
| 998 | |g 122976843 |a Comba, Peter |m 122976843:Comba, Peter |d 120000 |d 120200 |e 120000PC122976843 |e 120200PC122976843 |k 0/120000/ |k 1/120000/120200/ |p 9 | ||
| 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 7 | ||
| 998 | |g 123258634 |a Trapp, Oliver |m 123258634:Trapp, Oliver |d 120000 |d 120100 |e 120000PT123258634 |e 120100PT123258634 |k 0/120000/ |k 1/120000/120100/ |p 6 | ||
| 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 5 | ||
| 998 | |g 1073900223 |a Wysocki, Jędrzej |m 1073900223:Wysocki, Jędrzej |d 120000 |d 120100 |e 120000PW1073900223 |e 120100PW1073900223 |k 0/120000/ |k 1/120000/120100/ |p 3 | ||
| 998 | |g 1159789681 |a Hermsen, Marko |m 1159789681:Hermsen, Marko |d 120000 |d 120100 |e 120000PH1159789681 |e 120100PH1159789681 |k 0/120000/ |k 1/120000/120100/ |p 2 | ||
| 998 | |g 1161017607 |a Gallardo-Donaire, Joan |m 1161017607:Gallardo-Donaire, Joan |d 120000 |d 120100 |e 120000PG1161017607 |e 120100PG1161017607 |k 0/120000/ |k 1/120000/120100/ |p 1 |x j | ||
| 999 | |a KXP-PPN157631104X |e 3012587519 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"origin":[{"dateIssuedDisp":"2018","dateIssuedKey":"2018"}],"relHost":[{"corporate":[{"role":"aut","roleDisplay":"VerfasserIn","display":"American Chemical Society"}],"origin":[{"dateIssuedKey":"1879","dateIssuedDisp":"1879-","publisherPlace":"Washington, DC ; Washington, DC","publisher":"ACS Publications ; American Chemical Society"}],"language":["eng"],"disp":"American Chemical SocietyJournal of the American Chemical Society","note":["Gesehen am 25.08.2020"],"name":{"displayForm":["Ed.: Allen J. Bard [u.a.]"]},"pubHistory":["1.1879 -"],"id":{"eki":["268132836"],"zdb":["1472210-0"],"issn":["1520-5126"]},"recId":"268132836","titleAlt":[{"title":"JACS"},{"title":"web edition"}],"title":[{"subtitle":"JACS","title":"Journal of the American Chemical Society","title_sort":"Journal of the American Chemical Society"}],"type":{"media":"Online-Ressource","bibl":"periodical"},"part":{"text":"140(2018), 1, Seite 355-361","extent":"7","volume":"140","issue":"1","pages":"355-361","year":"2018"}}],"physDesc":[{"extent":"7 S."}],"note":["Published: December 1, 2017","Gesehen am 13.06.2018"],"language":["eng"],"recId":"157631104X","id":{"doi":["10.1021/jacs.7b10496"],"eki":["157631104X"]},"name":{"displayForm":["Joan Gallardo-Donaire, Marko Hermsen, Jedrzej Wysocki, Martin Ernst, Frank Rominger, Oliver Trapp, A. Stephen K. Hashmi, Ansgar Schäfer, Peter Comba, and Thomas Schaub"]},"person":[{"family":"Gallardo-Donaire","roleDisplay":"VerfasserIn","display":"Gallardo-Donaire, Joan","given":"Joan","role":"aut"},{"family":"Hermsen","roleDisplay":"VerfasserIn","given":"Marko","display":"Hermsen, Marko","role":"aut"},{"family":"Wysocki","roleDisplay":"VerfasserIn","display":"Wysocki, Jędrzej","given":"Jędrzej","role":"aut"},{"role":"aut","family":"Rominger","roleDisplay":"VerfasserIn","given":"Frank","display":"Rominger, Frank"},{"display":"Trapp, Oliver","roleDisplay":"VerfasserIn","given":"Oliver","family":"Trapp","role":"aut"},{"family":"Hashmi","roleDisplay":"VerfasserIn","given":"A. Stephen K.","display":"Hashmi, A. Stephen K.","role":"aut"},{"role":"aut","family":"Comba","roleDisplay":"VerfasserIn","given":"Peter","display":"Comba, Peter"},{"family":"Schaub","roleDisplay":"VerfasserIn","given":"Thomas","display":"Schaub, Thomas","role":"aut"}],"type":{"bibl":"article-journal","media":"Online-Ressource"},"title":[{"title_sort":"Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen","title":"Direct asymmetric ruthenium-catalyzed reductive amination of alkyl-aryl ketones with ammonia and hydrogen"}]} | ||
| SRT | |a GALLARDODODIRECTASYM2018 | ||