Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans
Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-D...
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MDPI AG
2020-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/1/97 |
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| author | Yuki Kitamura Yuki Murata Mizuki Iwai Mio Matsumura Shuji Yasuike |
| author_facet | Yuki Kitamura Yuki Murata Mizuki Iwai Mio Matsumura Shuji Yasuike |
| author_sort | Yuki Kitamura |
| collection | DOAJ |
| description | Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)<sub>2</sub> and 2 eq. of CuCl<sub>2</sub> at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity than an electron-withdrawing group. Single crystal X-ray analysis of tri(<i>p</i>-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bipyramidal geometry. |
| first_indexed | 2024-03-10T13:44:01Z |
| format | Article |
| id | doaj.art-dd7940c620f94100affb301a0a0a5939 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T13:44:01Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-dd7940c620f94100affb301a0a0a59392023-11-21T02:50:24ZengMDPI AGMolecules1420-30492020-12-012619710.3390/molecules26010097Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-ArylbenzofuransYuki Kitamura0Yuki Murata1Mizuki Iwai2Mio Matsumura3Shuji Yasuike4School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanSchool of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, JapanPd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)<sub>2</sub> and 2 eq. of CuCl<sub>2</sub> at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity than an electron-withdrawing group. Single crystal X-ray analysis of tri(<i>p</i>-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bipyramidal geometry.https://www.mdpi.com/1420-3049/26/1/97C–H arylationpalladium catalystantimonytriarylantimony difluoridebenzofuran |
| spellingShingle | Yuki Kitamura Yuki Murata Mizuki Iwai Mio Matsumura Shuji Yasuike Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans Molecules C–H arylation palladium catalyst antimony triarylantimony difluoride benzofuran |
| title | Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans |
| title_full | Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans |
| title_fullStr | Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans |
| title_full_unstemmed | Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans |
| title_short | Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans |
| title_sort | palladium catalyzed c h arylation of benzofurans with triarylantimony difluorides for the synthesis of 2 arylbenzofurans |
| topic | C–H arylation palladium catalyst antimony triarylantimony difluoride benzofuran |
| url | https://www.mdpi.com/1420-3049/26/1/97 |
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