Gold meets selenium: dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights
Herein, we report the synthesis of seleno-substituted chromenes from selenoalkynes and phenols. In this cascade reaction, the applied gold catalyst not only functions as a π-acid, but also as a Lewis acid, enabling the propargylic substitution in the first step to connect the oxygen carbon bond. Und...
Gespeichert in:
| Hauptverfasser: | , , , , , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
November 7, 2024
|
| In: |
Chemistry - a European journal
Year: 2024, Jahrgang: 30, Heft: 62, Pages: 1-7 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202402426 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202402426 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202402426 
|
| Verfasserangaben: | Eric F. Lopes, Martin C. Dietl, Benjamin Ziegler, Matthias Rudolph, Thiago Barcellos, Thomas Oeser, Diogo S. Lüdtke, and A. Stephen K. Hashmi |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1921161442 | ||
| 003 | DE-627 | ||
| 005 | 20250717004308.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 250402s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/chem.202402426 |2 doi | |
| 035 | |a (DE-627)1921161442 | ||
| 035 | |a (DE-599)KXP1921161442 | ||
| 035 | |a (OCoLC)1528043934 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Lopes, Eric F. |e VerfasserIn |0 (DE-588)1324457104 |0 (DE-627)1884324541 |4 aut | |
| 245 | 1 | 0 | |a Gold meets selenium |b dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights |c Eric F. Lopes, Martin C. Dietl, Benjamin Ziegler, Matthias Rudolph, Thiago Barcellos, Thomas Oeser, Diogo S. Lüdtke, and A. Stephen K. Hashmi |
| 264 | 1 | |c November 7, 2024 | |
| 300 | |b Illustrationen | ||
| 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 Online verfügbar: 19. August 2024 | ||
| 500 | |a Gesehen am 02.04.2025 | ||
| 520 | |a Herein, we report the synthesis of seleno-substituted chromenes from selenoalkynes and phenols. In this cascade reaction, the applied gold catalyst not only functions as a π-acid, but also as a Lewis acid, enabling the propargylic substitution in the first step to connect the oxygen carbon bond. Under the optimal reaction condition a total of 26 chromenes were accessible by this modular access. During scale up experiments, the hydrolysis of the vinylselenium substructure to the corresponding chromenones was observed. By revisiting the electron-rich starting materials, four chromenones were produced following a one-pot reaction using a single gold catalyst. To better understand the interaction of gold and selenium, a series of nuclear magnetic resonance studies and high-resolution mass spectrometry studies were performed, which led to the proposal of a mechanism for this transformation. | ||
| 650 | 4 | |a Catalysis | |
| 650 | 4 | |a Dual activation | |
| 650 | 4 | |a Gold | |
| 650 | 4 | |a Lewis acid | |
| 650 | 4 | |a Selenium | |
| 700 | 1 | |a Dietl, Martin C. |d 1994- |e VerfasserIn |0 (DE-588)1165526328 |0 (DE-627)1029459606 |0 (DE-576)510403670 |4 aut | |
| 700 | 1 | |a Ziegler, Benjamin |e VerfasserIn |0 (DE-588)1362106259 |0 (DE-627)1921162449 |4 aut | |
| 700 | 1 | |a Rudolph, Matthias |d 1975- |e VerfasserIn |0 (DE-588)136790380 |0 (DE-627)587252405 |0 (DE-576)301277524 |4 aut | |
| 700 | 1 | |a Barcellos, Thiago |e VerfasserIn |4 aut | |
| 700 | 1 | |a Oeser, Thomas |e VerfasserIn |0 (DE-588)1025249038 |0 (DE-627)721919715 |0 (DE-576)170725553 |4 aut | |
| 700 | 1 | |a Lüdtke, Diogo S. |e VerfasserIn |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 | |
| 773 | 0 | 8 | |i Enthalten in |t Chemistry - a European journal |d Weinheim : Wiley-VCH, 1995 |g 30(2024), 62, Artikel-ID e202402426, Seite 1-7 |h Online-Ressource |w (DE-627)270935193 |w (DE-600)1478547-X |w (DE-576)078707404 |x 1521-3765 |7 nnas |a Gold meets selenium dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights |
| 773 | 1 | 8 | |g volume:30 |g year:2024 |g number:62 |g elocationid:e202402426 |g pages:1-7 |g extent:7 |a Gold meets selenium dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights |
| 856 | 4 | 0 | |u https://doi.org/10.1002/chem.202402426 |x Verlag |x Resolving-System |z kostenfrei |3 Volltext |
| 856 | 4 | 0 | |u https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202402426 |x Verlag |z kostenfrei |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20250402 | ||
| 993 | |a Article | ||
| 998 | |g 101199576X |a Hashmi, A. Stephen K. |m 101199576X:Hashmi, A. Stephen K. |d 120000 |e 120000PH101199576X |k 0/120000/ |p 8 |y j | ||
| 998 | |g 1025249038 |a Oeser, Thomas |m 1025249038:Oeser, Thomas |d 120000 |d 120100 |e 120000PO1025249038 |e 120100PO1025249038 |k 0/120000/ |k 1/120000/120100/ |p 6 | ||
| 998 | |g 136790380 |a Rudolph, Matthias |m 136790380:Rudolph, Matthias |d 120000 |d 120100 |e 120000PR136790380 |e 120100PR136790380 |k 0/120000/ |k 1/120000/120100/ |p 4 | ||
| 998 | |g 1362106259 |a Ziegler, Benjamin |m 1362106259:Ziegler, Benjamin |d 120000 |e 120000PZ1362106259 |k 0/120000/ |p 3 | ||
| 998 | |g 1165526328 |a Dietl, Martin C. |m 1165526328:Dietl, Martin C. |d 120000 |d 120100 |e 120000PD1165526328 |e 120100PD1165526328 |k 0/120000/ |k 1/120000/120100/ |p 2 | ||
| 999 | |a KXP-PPN1921161442 |e 4696490289 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"name":{"displayForm":["Eric F. Lopes, Martin C. Dietl, Benjamin Ziegler, Matthias Rudolph, Thiago Barcellos, Thomas Oeser, Diogo S. Lüdtke, and A. Stephen K. Hashmi"]},"recId":"1921161442","note":["Online verfügbar: 19. August 2024","Gesehen am 02.04.2025"],"language":["eng"],"origin":[{"dateIssuedDisp":"November 7, 2024","dateIssuedKey":"2024"}],"id":{"eki":["1921161442"],"doi":["10.1002/chem.202402426"]},"relHost":[{"disp":"Gold meets selenium dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insightsChemistry - a European journal","origin":[{"publisher":"Wiley-VCH","dateIssuedDisp":"1995-","dateIssuedKey":"1995","publisherPlace":"Weinheim"}],"part":{"extent":"7","year":"2024","volume":"30","text":"30(2024), 62, Artikel-ID e202402426, Seite 1-7","pages":"1-7","issue":"62"},"language":["eng"],"note":["Fortsetzung der Druck-Ausgabe","Gesehen am 27. Februar 2017"],"recId":"270935193","title":[{"title":"Chemistry - a European journal","title_sort":"Chemistry - a European journal"}],"physDesc":[{"extent":"Online-Ressource"}],"type":{"bibl":"periodical","media":"Online-Ressource"},"id":{"zdb":["1478547-X"],"issn":["1521-3765"],"doi":["10.1002/(ISSN)1521-3765"],"eki":["270935193"]},"pubHistory":["1.1995 -"]}],"title":[{"title":"Gold meets selenium","title_sort":"Gold meets selenium","subtitle":"dual activation of selenium-containing propargyl alcohols towards the synthesis of 2H-chromenes and mechanistic insights"}],"physDesc":[{"extent":"7 S.","noteIll":"Illustrationen"}],"type":{"bibl":"article-journal","media":"Online-Ressource"},"person":[{"family":"Lopes","display":"Lopes, Eric F.","role":"aut","given":"Eric F."},{"given":"Martin C.","role":"aut","display":"Dietl, Martin C.","family":"Dietl"},{"family":"Ziegler","display":"Ziegler, Benjamin","role":"aut","given":"Benjamin"},{"given":"Matthias","role":"aut","display":"Rudolph, Matthias","family":"Rudolph"},{"family":"Barcellos","display":"Barcellos, Thiago","role":"aut","given":"Thiago"},{"display":"Oeser, Thomas","family":"Oeser","given":"Thomas","role":"aut"},{"display":"Lüdtke, Diogo S.","family":"Lüdtke","given":"Diogo S.","role":"aut"},{"role":"aut","given":"A. Stephen K.","family":"Hashmi","display":"Hashmi, A. Stephen K."}]} | ||
| SRT | |a LOPESERICFGOLDMEETSS7202 | ||