103441-67-4Relevant articles and documents
General preparation of functionalized o-nitroarylmagnesium halides through an iodine-magnesium exchange
Sapountzis, Ioannis,Knochel, Paul
, p. 1610 - 1611 (2002)
Highly functionalized aryl Grignard reagents with an ortho-nitro substituent have been synthesized from 2-iodonitroaryl compounds through an I-Mg exchange reaction with PhMgCl or mesityl magnesium bromide (see scheme). These reagents are stable (T-20°C f
Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis
Akram, Manjur O.,Mali, Pramod S.,Patil, Nitin T.
, p. 3075 - 3078 (2017)
A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.
Palladium(0)-catalyzed intramolecular decarboxylative allylation of ortho nitrobenzoic esters
Hossian, Asik,Singha, Shantanu,Jana, Ranjan
, p. 3934 - 3937 (2014/08/18)
A Pd/Ag bimetallic system has been developed for the decarboxylative allylation of ortho-nitrobenzoic esters in an intramolecular fashion. In contrast to the typical sp2-sp3 cross-coupling approach which requires air and moisture sensitive preformed organometallic reagents, we provide an alternative route to the synthesis of ortho-allyl nitroarenes from the corresponding ortho-nitrobenzoic acid derivatives. The reaction proceeds through a mechanistically distinct decarboxylative metalation pathway. A cooperative reactivity of palladium and silver is crucial for the reaction outcome.
Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes
Nicolai, Stefano,Sedigh-Zadeh, Raha,Waser, Jeroime
, p. 3783 - 3801 (2013/06/26)
Tetrahydrofurans and pyrrolidines are among the most important heterocycles found in bioactive compounds. Cyclization-functionalization domino reactions of alcohols or amines onto olefins constitute one of the most efficient methods to access them. In this context, oxy- and aminoalkynylation are especially important reactions, because of the numerous transformations possible with the triple bond of acetylenes, yet these methods have been limited to the use of silyl protected acetylenes. Herein, we report the first palladium-catalyzed oxy- and aminoalkynylation using aliphatic bromoalkynes, which proceeded with high diastereoselectivity and functional group tolerance. A one-pot hydrogenation of the triple bond gave then access to alkyl-substituted tetrahydrofurans and pyrroldines. Finally, a detailed study of the side products formed during the reaction gave a first insight into the reaction mechanism.
Synthesis of a leucomitosane via a diastereoselective radical cascade
Brucelle, Francois,Renaud, Philippe
, p. 6245 - 6252 (2013/07/26)
The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones
The attempted stereoselective synthesis of chiral 2,2′-biindoline
Gresser, Mary J.,Wales, Steven M.,Keller, Paul A.
experimental part, p. 6965 - 6976 (2010/09/18)
The attempted first stereoselective synthesis of 2,2′-biindoline using a metathesis-Sharpless asymmetric dihydroxylation strategy results in the synthesis of the heterocycle in poor to modest stereoselectivity. Attempts to improve the ee by varying the he
Highly stereoselective 7-endo-trig /ring contraction cascade to construct pyrrolo[1,2- a ]quinoline derivatives
Li, Xinyu,Li, Cheng,Zhang, Wenjing,Lu, Xiang,Han, Shiqing,Hong, Ran
supporting information; experimental part, p. 1696 - 1699 (2010/09/05)
With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the γ-lactam ring and electron-rich arene are important driving forces for ring contraction.
Synthesis of functionalized nitroarylmagnesium halides via an iodine-magnesium exchange
Sapountzis, Ioannis,Dube, Henry,Lewis, Robert,Gommermann, Nina,Knochel, Paul
, p. 2445 - 2454 (2007/10/03)
(Chemical Equation Presented) Various nitro-substituted aryl and heteroaryl iodides undergo an iodine-magnesium exchange reaction when treated with PhMgCl leading to nitro-containing magnesium organometallics. These Grignard reagents display an excellent stability at temperatures below -40°C and do not undergo electron-transfer reactions. They react as expected with various electrophiles.
The reactivity of polyfunctionalized iminophosphoranes
Carite,Alazard,Ogino,Thal
, p. 7011 - 7014 (2007/10/02)
The reactivity of some functionalized azides has been studied under the conditions of the Staudinger and aza-Wittig reactions. With the azides having a trifluoroacetamido group in the ortho-position of the aromatic ring, intramolecular reactions have been observed which allow new synthetic approaches to indoline and imidazoindole compounds.
