Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides
S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2013-03-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.50 |
| _version_ | 1818451139811606528 |
|---|---|
| author | Silvia M. Soria-Castro Alicia B. Peñéñory |
| author_facet | Silvia M. Soria-Castro Alicia B. Peñéñory |
| author_sort | Silvia M. Soria-Castro |
| collection | DOAJ |
| description | S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields. |
| first_indexed | 2024-12-14T21:02:27Z |
| format | Article |
| id | doaj.art-9115e41a21924bf0baebbb0895ac791d |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T21:02:27Z |
| publishDate | 2013-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9115e41a21924bf0baebbb0895ac791d2022-12-21T22:47:33ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-03-019146747510.3762/bjoc.9.501860-5397-9-50Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfidesSilvia M. Soria-Castro0Alicia B. Peñéñory1INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA. Córdoba, Argentina, Fax: (+54) 351-4333030INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA. Córdoba, Argentina, Fax: (+54) 351-4333030S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.https://doi.org/10.3762/bjoc.9.50catalysiscoppercross-couplingpotassium thioacetatesulfur heterocycles |
| spellingShingle | Silvia M. Soria-Castro Alicia B. Peñéñory Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides Beilstein Journal of Organic Chemistry catalysis copper cross-coupling potassium thioacetate sulfur heterocycles |
| title | Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides |
| title_full | Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides |
| title_fullStr | Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides |
| title_full_unstemmed | Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides |
| title_short | Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides |
| title_sort | efficient cu catalyzed base free c s coupling under conventional and microwave heating a simple access to s heterocycles and sulfides |
| topic | catalysis copper cross-coupling potassium thioacetate sulfur heterocycles |
| url | https://doi.org/10.3762/bjoc.9.50 |
| work_keys_str_mv | AT silviamsoriacastro efficientcucatalyzedbasefreecscouplingunderconventionalandmicrowaveheatingasimpleaccesstosheterocyclesandsulfides AT aliciabpenenory efficientcucatalyzedbasefreecscouplingunderconventionalandmicrowaveheatingasimpleaccesstosheterocyclesandsulfides |