Palladium-Catalyzed Dearomative Heck/C(sp2)-H Activation/Decarboxylative Cyclization of C2-Tethered Indoles
Shuyi Guo1, Wenbo Deng1, Xiaochang Xiao1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081, China.
Abstract:
Until now, palladium-catalyzed dearomative Heck reactions of indoles were largely limited to β-H elimination and nucleophilic capture of the transient alkyl-Pd(II) species. Herein, we disclose a novel palladium-catalyzed dearomative Heck/C(sp2)-H activation/decarboxylative cyclization of C2-tethered indoles. In this protocol, the alkyl-Pd(II) species formed by dearomatization of C2-tethered indoles is not terminated by common β-H elimination or nucleophilic capture, but rather generates C,C-palladacycle via C-H activation. The latter is intercepted by α-bromoacrylic acids to produce pentacyclic and heptacyclic fused indolines.
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