Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide
The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated...
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| Format: | Article |
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Beilstein-Institut
2013-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.9.277 |
| _version_ | 1819115747405725696 |
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| author | Yuzo Nakamura Motohiro Fujiu Tatsuya Murase Yoshimitsu Itoh Hiroki Serizawa Kohsuke Aikawa Koichi Mikami |
| author_facet | Yuzo Nakamura Motohiro Fujiu Tatsuya Murase Yoshimitsu Itoh Hiroki Serizawa Kohsuke Aikawa Koichi Mikami |
| author_sort | Yuzo Nakamura |
| collection | DOAJ |
| description | The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert–Prakash reagents (CF3SiR3), are not required. |
| first_indexed | 2024-12-22T05:06:06Z |
| format | Article |
| id | doaj.art-ea6e6af4b4e2425e8575ba1b92730655 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T05:06:06Z |
| publishDate | 2013-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ea6e6af4b4e2425e8575ba1b927306552022-12-21T18:38:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-11-01912404240910.3762/bjoc.9.2771860-5397-9-277Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodideYuzo Nakamura0Motohiro Fujiu1Tatsuya Murase2Yoshimitsu Itoh3Hiroki Serizawa4Kohsuke Aikawa5Koichi Mikami6Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanDepartment of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-113 O-okayama, Meguro-ku, Tokyo 152-8552, JapanThe trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated products in moderate to high yields. The advantage of this method is that additives such as metal fluoride (MF), which are indispensable to activate silyl groups for transmetallation in the corresponding reactions catalyzed by copper salt by using the Ruppert–Prakash reagents (CF3SiR3), are not required.https://doi.org/10.3762/bjoc.9.277organo-fluorineRuppert–Prakash reagenttrifluoromethyltrifluoromethylationtrifluoromethyl zinc |
| spellingShingle | Yuzo Nakamura Motohiro Fujiu Tatsuya Murase Yoshimitsu Itoh Hiroki Serizawa Kohsuke Aikawa Koichi Mikami Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide Beilstein Journal of Organic Chemistry organo-fluorine Ruppert–Prakash reagent trifluoromethyl trifluoromethylation trifluoromethyl zinc |
| title | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| title_full | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| title_fullStr | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| title_full_unstemmed | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| title_short | Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| title_sort | cu catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide |
| topic | organo-fluorine Ruppert–Prakash reagent trifluoromethyl trifluoromethylation trifluoromethyl zinc |
| url | https://doi.org/10.3762/bjoc.9.277 |
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