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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Bibliographic Details
Published inOrganic letters Vol. 26; no. 21; pp. 4422 - 4426
Main Authors Zhang, Jinhui, Liu, Chao, Wu, Jiahao, Tan, Xiangwen, Wu, Wanqing, Jiang, Huanfeng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.05.2024
Amer Chemical Soc
Subjects
abscission
carbon-hydrogen bond activation
Chemistry
Chemistry, Organic
diastereoselectivity
Physical Sciences
Science & Technology
FUNCTIONALIZATION
LACTONES
CLEAVAGE
AMINES
TETRAHYDROQUINOLINES
CYCLIZATION
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.4c00880

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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c00880