Vidyasagar, Adiyala ; Shi, Jinwei ; Kreitmeier, Peter ; Reiser, Oliver 
Alternative Links zum Volltext:DOIVerlag
| Dokumentenart: | Artikel |
|---|
| Titel eines Journals oder einer Zeitschrift: | Organic Letters |
|---|
| Verlag: | AMER CHEMICAL SOC |
|---|
| Ort der Veröffentlichung: | WASHINGTON |
|---|
| Band: | 20 |
|---|
| Nummer des Zeitschriftenheftes oder des Kapitels: | 22 |
|---|
| Seitenbereich: | S. 6984-6989 |
|---|
| Datum: | 2018 |
|---|
| Institutionen: | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
|---|
| Identifikationsnummer: | | Wert | Typ |
|---|
| 10.1021/acs.orglett.8b02725 | DOI |
|
|---|
| Stichwörter / Keywords: | DEPENDENT KINASE INHIBITORS; SIMPLE INDOLE ALKALOIDS; C-H ARYLATION; 2,3-DISUBSTITUTED INDOLES; BIOLOGICAL EVALUATION; PHOTOREDOX CATALYSIS; ALPHA-BROMOCHALCONES; METAL-FREE; CYCLIZATION; DERIVATIVES; |
|---|
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
|---|
| Status: | Veröffentlicht |
|---|
| Begutachtet: | Ja, diese Version wurde begutachtet |
|---|
| An der Universität Regensburg entstanden: | Ja |
|---|
| Dokumenten-ID: | 46598 |
|---|
Web of Science
Zusammenfassung
A visible-light-mediated radical tandem cyclization of ortho-isocyano-alpha-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C-C/C-S and C-O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron transfer from an a-carbonyl radical to the photocatalyst. This method allows preparation of diverse ...
Zusammenfassung
A visible-light-mediated radical tandem cyclization of ortho-isocyano-alpha-bromo cinnamates to 2-substituted indole-3-glyoxylates is achieved by formation of both C-C/C-S and C-O bonds. The reaction proceeds through a hitherto unprecedented bromine- or methoxy-group-promoted umpolung back electron transfer from an a-carbonyl radical to the photocatalyst. This method allows preparation of diverse 2-arylated or 2-thioarylated indole-3-glyoxylates. The glyoxylate group installed in the products can be utilized for several biologically relevant manipulations.
Altmetric