183789-20-0Relevant articles and documents
Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
supporting information, p. 183 - 187 (2018/01/17)
Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues
Hédouin, Jonathan,Schneider, Cédric,Gillaizeau, Isabelle,Hoarau, Christophe
supporting information, p. 6027 - 6032 (2018/10/05)
Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C-H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, i
Harnessing [1,4], [1,5], and [1,6] Anionic Fries-type Rearrangements by Reaction-Time Control in Flow
Kim, Heejin,Inoue, Keita,Yoshida, Jun-Ichi
supporting information, p. 7863 - 7866 (2017/06/27)
A series of anionic Fries-type rearrangements of carbamoyl-substituted aryllithium intermediates were controlled by using flow microreactor systems. For the [1,4] and [1,5] rearrangements, the aryllithium intermediate formed before carbamoyl migration and
Synthesis and Properties of Functional Twisted Tolanes
Kozhemyakin, Yury,Kretzschmar, Andreas,Kr?mer, Maximilian,Rominger, Frank,Dreuw, Andreas,Bunz, Uwe H. F.
, p. 9908 - 9918 (2017/07/25)
The synthesis and optical properties of several novel fluorescent and/or phosphorescent bridged tolanes (tolanophanes) are reported and their optical and structural properties are investigated. Specifically, diiodinated and bisalkynylated tolanophanes were obtained, and characterized by spectroscopy and computational methods. They represent attractive building blocks for novel polymers and emissive solid-state materials.
Synthesis of Functionalized Alkylidene Indanes and Indanones through Tandem Phosphine-Palladium Catalysis
Fan, Yi Chiao,Kwon, Ohyun
supporting information, p. 2058 - 2061 (2015/05/20)
Densely functionalized alkylidene indanes and indanones can be prepared efficiently in one pot, in high yields with good stereoselectivities (in some cases exclusively the Z-isomer), through a route involving phosphine-catalyzed Michael addition followed
One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade
Zheng, Zhitong,Tu, Huangfei,Zhang, Liming
supporting information, p. 2445 - 2448 (2014/03/21)
A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields. A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields (see scheme). Copyright
Cyclization of η3-benzylpalladium intermediates derived from carbene insertion
Gutman, Eugene S.,Arredondo, Vanessa,Van Vranken, David L.
supporting information, p. 5498 - 5501 (2015/01/09)
Migratory insertion of benzylidene carbene ligands into arylpalladium(II) species generates η3-benzylpalladium intermediates that can cyclize to generate five- and six-membered rings with new sp3 centers. The reaction tolerates a ran
Facile synthesis of [1,2,3]-triazole-fused isoindolines, tetrahydroisoquinolines, benzoazepines and benzoazocines by palladium-copper catalysed heterocyclisation
Brahma, Kaushik,Achari, Basudeb,Chowdhury, Chinmay
supporting information, p. 545 - 555 (2013/04/10)
An elegant method for the synthesis of 1,2,3-triazoles fused with five-, six-, seven- and eight-membered benzoheterocycles, including isoindoline, tetrahydroisoquinoline, benzoazepine and benzoazocine, has been developed via palladium-copper catalysed reactions in one-pot. The broad scope of this reaction was illustrated by effecting bis-heteroannulations, synthesis of uracil derivatives of biological interest, and employment of acetylene gas as an inexpensive substrate. The reactions are experimentally simple and utilise easily accessible substrates of different types. Georg Thieme Verlag Stuttgart · New York.
Efficient procedures to prepare primary and secondary alkyl halides from alkanols via the corresponding sulfonates under mild conditions
Cahiez, Gerard,Gager, Olivier,Moyeux, Alban,Delacroix, Thomas
supporting information; experimental part, p. 1519 - 1528 (2012/07/03)
The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C-H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction. Copyright
Novel cyclization cascades to functionalized indanes and tetrahydronaphthalenes
Khan, Zulfiqar A.,Iwaoka, Michio,Wirth, Thomas
experimental part, p. 6639 - 6646 (2010/10/19)
Cyclization cascades involving C-C bond formations followed by lactonization reactions provide fast access to structurally complex tricyclic indane and tetrahydronaphthalene derivatives. Crown Copyright