- Iptycenes with an acridinone motif developed through [4+2] cycloaddition of tethered naphthalene and iminoquinone: Via a radical reaction
-
A new class of iptycenes was developed by combining 2-(naphthalen-1-yl)anilines and p-benzoquinones through copper(ii)-mediated radical cyclisation. This unusual cyclisation reaction resulted in the robust and efficient syntheses of iptycenes with an acridinone motif. These iptycenes can be further transformed into planar acridinone heterocyclics through the Diels-Alder reaction.
- Raju, Selvam,Annamalai, Pratheepkumar,Chen, Pei-Ling,Liu, Yi-Hung,Chuang, Shih-Ching
-
-
Read Online
- Synthesis of cyclopenta-fused polycyclic aromatic hydrocarbons utilizing aryl-substituted anilines
-
Cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs), potentially electronically and biologically highly active materials, were synthesized from readily available 2-aryl-substituted anilines. Reactions occur under extremely mild, room temperature conditions using tBuONO as the sole reagent. The use of a nitrite source generates a reactive diazonium intermediate in situ that then reacts with a tethered polycyclic aromatic moiety by intramolecular aromatic substitution. This protocol could be presented as one of the simplest methods to access CP-PAHs.
- Choi, Yeojin,Chatterjee, Tanmay,Kim, Jun,Kim, Jun Soo,Cho, Eun Jin
-
p. 6804 - 6810
(2016/07/23)
-
- Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents
-
A direct transformation of carboxylic acid esters into arenes with 1,5-bifunctional organomagnesium reagents is described. This efficient and practical method enables the one-step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5-organodimagnesium reagent to the ester is followed by an immediate 1,4-elimination reaction that leads to the direct [5+1] formation of a new aromatic ring.
- Link, Achim,Fischer, Christian,Sparr, Christof
-
supporting information
p. 12163 - 12166
(2015/10/12)
-
- A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins
-
We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90% yield and up to 84% ee under optimized conditions.
- Gao, Ying-Xiang,Chang, Le,Shi, Hang,Liang, Bo,Wongkhan, Kittiya,Chaiyaveij, Duangduan,Batsanov, Andrei S.,Marder, Todd B.,Li, Chuang-Chuang,Yang, Zhen,Huanga, Yong
-
supporting information; experimental part
p. 1955 - 1966
(2010/11/03)
-