A photochemical dehydrogenative strategy for aniline synthesis was written by U. Dighe, Shashikant;Julia, Fabio;Luridiana, Alberto;Douglas, James J.;Leonori, Daniele. And the article was included in Nature (London, United Kingdom) in 2020.Application In Synthesis of 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one This article mentions the following:
Chem. reactions that reliably join two mol. fragments together (cross-couplings) are essential to the discovery and manufacture of pharmaceuticals and agrochems.1,2. The introduction of amines onto functionalized aromatics at specific and pre-determined positions (ortho vs. meta vs. para) is currently achievable only in transition-metal-catalyzed processes and requires halogen- or boron-containing substrates3-6. The introduction of these groups around the aromatic unit is dictated by the intrinsic reactivity profile of the method (electrophilic halogenation or C-H borylation) so selective targeting of all positions is often not possible. Here we report a non-canonical cross-coupling approach for the construction of anilines, exploiting saturated cyclohexanones as aryl electrophile surrogates. Condensation between amines and carbonyls, a process that frequently occurs in nature and is often used by (bio-)organic chemists7, enables a predetermined and site-selective carbon-nitrogen (C-N) bond formation, while a photoredox- and cobalt-based catalytic system progressively desaturates the cyclohexene ring en route to the aniline. Given that functionalized cyclohexanones are readily accessible with complete regiocontrol using the well established carbonyl reactivity, this approach bypasses some of the frequent selectivity issues of aromatic chem. We demonstrate the utility of this C-N coupling protocol by preparing com. medicines and by the late-stage amination-aromatization of natural products, steroids and terpene feedstocks. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one (cas: 120014-30-4Application In Synthesis of 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one).
5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one (cas: 120014-30-4) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Application In Synthesis of 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem