A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds
A fast and efficient palladium-catalyzed fourfold domino Sonogashira/double-carbopalladation/C H-activation reaction that converts simple aromatic systems into complex polycyclic hydrocarbons has been developed. A number of substituted products has thus been prepared in yields up to 89 %. The structural assignment has been confirmed by using single-crystal X-ray crystallography. The products show intriguing fluorescence activity and thus might serve as chemical sensors or fluorescent imaging dyes.
Tietze, Lutz F.,Eichhorst, Christoph,Hungerland, Tim,Steinert, Markus
Intramolecular Aryl Migration of Diaryliodonium Salts: Access to ortho-Iodo Diaryl Ethers
By using vicinal trifluoromethanesulfonate-substituted diaryliodonium salts, a novel approach was developed for the synthesis of ortho-iodo diaryl ethers by intramolecular aryl migration. The reaction conditions are mild with a broad substrate scope. Mechanistic insight suggests a sulfonyl-directed nucleophilic aromatic substitution pathway. Additionally, the product ortho-iodo diaryl ethers serve as versatile synthons as demonstrated with several coupling reactions. Furthermore, a useful thyroxine analogue of the 3-iodo-l-thyronine (3-T1) derivative was synthesized by this aryl migration procedure.
Chen, Huangguan,Han, Jianwei,Wang, Limin
supporting information
p. 12313 - 12317
(2018/09/10)
Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches
A highly efficient palladium-catalyzed fourfold tandem-domino reaction consisting of two carbopalladation and two C-H-activation steps was developed for the synthesis of two types of tetrasubstituted alkenes 3 and 6 with intrinsic helical chirality starting from substrates 1 and 4, respectively. A sixfold tandem-domino reaction was also developed by including a Sonogashira reaction. 20 compounds with different substitution patterns were prepared with yields of up to 97%. Structure elucidation by X-ray crystallography confirmed helical chirality of the two alkene moieties. Photophysical investigations of some of the compounds showed pronounced switching properties through light-controlled changes of their stereochemical configuration.
A facile synthesis of 3-substituted benzofurans and indoles through a palladium-catalyzed domino carbopalladation/CH-activation/isomerization process
Novel benzofurans 7 and indoles 8 have been prepared from 3 and 4 by a Pd-catalyzed mono-component three-fold domino carbopalladation/CH-activation/ isomerization process and from 12 and 5 to give 8 by a two-component fourfold domino Sonogashira/carbopall
Tietze, Lutz F.,Hungerland, Tim,Ammermann, Jonas,Eichhorst, Christoph,Reichmann, Sven O.,Stalke, Dietmar
p. 1537 - 1555
(2014/01/17)
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