Palladium-Catalyzed Annulation of Tertiary Anilines with 3‑Butenoic Acid via Dual C–H Bond Activation
Catalytic cyclization via dual C–H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp3)–H and ortho-C(sp2)–H activation is described. The remarkable characteri...
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| Published in | Organic letters Vol. 26; no. 21; pp. 4422 - 4426 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
31.05.2024
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.4c00880 |
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| Abstract | Catalytic cyclization via dual C–H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp3)–H and ortho-C(sp2)–H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C–H bond abscission is not the turnover-limiting step. |
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| AbstractList | Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp³)-H and ortho-C(sp²)-H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C-H bond abscission is not the turnover-limiting step. Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-alpha-C(sp(3))-H and ortho-C(sp(2))-H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C-H bond abscission is not the turnover-limiting step. Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp3)-H and ortho-C(sp2)-H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C-H bond abscission is not the turnover-limiting step.Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp3)-H and ortho-C(sp2)-H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C-H bond abscission is not the turnover-limiting step. Catalytic cyclization via dual C–H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via N-α-C(sp3)–H and ortho-C(sp2)–H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C–H bond abscission is not the turnover-limiting step. Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed annulation of tertiary anilines with 3-butenoic acid via -α-C(sp )-H and -C(sp )-H activation is described. The remarkable characteristics of this reaction include excellent diastereoselectivity, broad substrate scope, and good tolerance for some highly sensitive groups. In addition, the KIE experiment suggested that the C-H bond abscission is not the turnover-limiting step. |
| Author | Jiang, Huanfeng Liu, Chao Zhang, Jinhui Wu, Wanqing Wu, Jiahao Tan, Xiangwen |
| AuthorAffiliation | Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering |
| AuthorAffiliation_xml | – name: Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering |
| Author_xml | – sequence: 1 givenname: Jinhui surname: Zhang fullname: Zhang, Jinhui – sequence: 2 givenname: Chao surname: Liu fullname: Liu, Chao – sequence: 3 givenname: Jiahao surname: Wu fullname: Wu, Jiahao – sequence: 4 givenname: Xiangwen surname: Tan fullname: Tan, Xiangwen – sequence: 5 givenname: Wanqing orcidid: 0000-0001-5151-7788 surname: Wu fullname: Wu, Wanqing email: cewuwq@scut.edu.cn – sequence: 6 givenname: Huanfeng orcidid: 0000-0002-4355-0294 surname: Jiang fullname: Jiang, Huanfeng email: jianghf@scut.edu.cn |
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| Keywords | FUNCTIONALIZATION LACTONES CLEAVAGE AMINES TETRAHYDROQUINOLINES CYCLIZATION |
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| Snippet | Catalytic cyclization via dual C–H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed... Catalytic cyclization via dual C-H bond activation has evolved as a powerful strategy for building bi- and polycyclic molecules. Herein, a palladium-catalyzed... |
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| SubjectTerms | abscission carbon-hydrogen bond activation Chemistry Chemistry, Organic diastereoselectivity Physical Sciences Science & Technology |
| Title | Palladium-Catalyzed Annulation of Tertiary Anilines with 3‑Butenoic Acid via Dual C–H Bond Activation |
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