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Electronic effect directed Au(I)-catalyzed cyclic C2-H bond functionalization of 3-allenylindoles
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China, Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University , 3663 North Zhongshan Lu, Shanghai 200062, P. R. China, and Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University , Hangzhou 310027, Zhejiang, P. R. China.
Abstract:
Gold-catalyzed cyclization reactions of indoles with an electron-deficient allene at the 3-position led to formation of dihydrocyclopenta[b]indole derivatives in moderate to excellent yields via C2-H bond functionalization of the indole unit. The presence of the electron-withdrawing alkoxycarbonyl, dialkoxyphosphono, or phenyl is crutial for this transformation. The potential synthetic dihydrocyclopenta[b]indole with the electron-withdrawing group has been demonstrated by applying a [3 + 2] cycloaddition reaction to construct the tretracycloskeleton.
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