Regiodivergent Metal-Catalyzed Oxidative Alkynylation of 2‑Arylthiazoles with Terminal Alkynes under Air Conditions
Regiodivergent transition-metal-catalyzed oxidative C5- and ortho-alkynylation of 2-arylthiazoles have been demonstrated. Namely, Pd(II)-catalysis selectively generated C5-alkynylated products from the reaction of 2-arylthiazoles and terminal alkynes. In contrast, Ru(II)-catalysis exclusively prov...
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| Veröffentlicht in: | Journal of organic chemistry 2024-08, Vol.89 (15), p.10953-10964 |
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| container_issue | 15 |
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| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Zhou, Pengfei Wang, Cheng Wan, Guibin Zheng, Weining Wei, Zongwu Liang, Taoyuan Jiang, Jun Zhang, Zhuan |
| description | Regiodivergent transition-metal-catalyzed oxidative C5- and ortho-alkynylation of 2-arylthiazoles have been demonstrated. Namely, Pd(II)-catalysis selectively generated C5-alkynylated products from the reaction of 2-arylthiazoles and terminal alkynes. In contrast, Ru(II)-catalysis exclusively provided ortho-alkynylated products from the same substrates. This protocol features a wide substrate scope, good functional group tolerance, high atom-economy, and exclusive regioselectivity. The alkynylated products can be readily converted into highly valuable synthons, which hold potential for applications in the fields of medicinal chemistry and materials science. |
| doi_str_mv | 10.1021/acs.joc.4c01381 |
| format | Article |
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Org. Chem</addtitle><date>2024-08-02</date><risdate>2024</risdate><volume>89</volume><issue>15</issue><spage>10953</spage><epage>10964</epage><pages>10953-10964</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>Regiodivergent transition-metal-catalyzed oxidative C5- and ortho-alkynylation of 2-arylthiazoles have been demonstrated. Namely, Pd(II)-catalysis selectively generated C5-alkynylated products from the reaction of 2-arylthiazoles and terminal alkynes. In contrast, Ru(II)-catalysis exclusively provided ortho-alkynylated products from the same substrates. This protocol features a wide substrate scope, good functional group tolerance, high atom-economy, and exclusive regioselectivity. 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| source | American Chemical Society Journals |
| subjects | air alkynes organic chemistry regioselectivity |
| title | Regiodivergent Metal-Catalyzed Oxidative Alkynylation of 2‑Arylthiazoles with Terminal Alkynes under Air Conditions |
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