93957-59-6Relevant articles and documents
C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations
Guo, Zi-Qiong,Xu, Hui,Wang, Xing,Wang, Zhen-Yu,Ma, Biao,Dai, Hui-Xiong
, p. 9716 - 9719 (2021/09/30)
C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.
Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions
Phipps, Robert J.,Grimster, Neil P.,Gaunt, Matthew J.
supporting information; experimental part, p. 8172 - 8174 (2009/02/02)
We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright
2-FORMYLATION OF 3-ARYLINDOLES
Walkup, R. E.,Linder, J.
, p. 2155 - 2158 (2007/10/02)
The preparation of N-substituted-3-(4-fluorophenyl)indoles (R = H, CH3, i-Pr) and their direct formylation at the 2-position by Vilsmeier-Haack or Friedel-Crafts methodologies is described.
