Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.
Ciccolini, C., Mari, G., Gatti, F.G., Gatti, G., Giorgi, G., Mantellini, F., et al. (2020). Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch. JOURNAL OF ORGANIC CHEMISTRY, 85(17), 11409-11425 [10.1021/acs.joc.0c01489].
Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
Giorgi G.;
2020-01-01
Abstract
Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
https://hdl.handle.net/11365/1117638
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