Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans
The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynyla...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2013-08-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.204 |
| _version_ | 1818652012671139840 |
|---|---|
| author | Yifan Li Jérôme Waser |
| author_facet | Yifan Li Jérôme Waser |
| author_sort | Yifan Li |
| collection | DOAJ |
| description | The direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP). |
| first_indexed | 2024-12-17T02:15:14Z |
| format | Article |
| id | doaj.art-2ac3356117b84d6695eff693d858a11d |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T02:15:14Z |
| publishDate | 2013-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-2ac3356117b84d6695eff693d858a11d2022-12-21T22:07:25ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-08-01911763176710.3762/bjoc.9.2041860-5397-9-204Zinc–gold cooperative catalysis for the direct alkynylation of benzofuransYifan Li0Jérôme Waser1Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH4306, 1015 Lausanne, SwitzerlandLaboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH4306, 1015 Lausanne, SwitzerlandThe direct alkynylation of benzofurans was achieved for the first time using the hypervalent iodine reagent 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) based on the cooperative effect between a gold catalyst and a zinc Lewis acid. High selectivity was observed for C2-alkynylation of benzofurans substituted with alkyl, aryl, halogen and ether groups. The reaction was also successful in the case of the more complex drug 8-methoxypsoralen (8-MOP).https://doi.org/10.3762/bjoc.9.204alkynylationbenzofuranscooperative catalysisdirect functionalizationgold catalysishypervalent iodine |
| spellingShingle | Yifan Li Jérôme Waser Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans Beilstein Journal of Organic Chemistry alkynylation benzofurans cooperative catalysis direct functionalization gold catalysis hypervalent iodine |
| title | Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans |
| title_full | Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans |
| title_fullStr | Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans |
| title_full_unstemmed | Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans |
| title_short | Zinc–gold cooperative catalysis for the direct alkynylation of benzofurans |
| title_sort | zinc gold cooperative catalysis for the direct alkynylation of benzofurans |
| topic | alkynylation benzofurans cooperative catalysis direct functionalization gold catalysis hypervalent iodine |
| url | https://doi.org/10.3762/bjoc.9.204 |
| work_keys_str_mv | AT yifanli zincgoldcooperativecatalysisforthedirectalkynylationofbenzofurans AT jeromewaser zincgoldcooperativecatalysisforthedirectalkynylationofbenzofurans |