42117-23-7Relevant academic research and scientific papers
Direct and Unified Access to Carbon Radicals from Aliphatic Alcohols by Cost-Efficient Titanium-Mediated Homolytic C?OH Bond Cleavage
Suga, Takuya,Takahashi, Yuuki,Miki, Chinatsu,Ukaji, Yutaka
supporting information, (2022/01/31)
Low-valent Ti-mediated homolytic C?O bond cleavage offers unified access to carbon radicals from ubiquitous non-activated tertiary, secondary, and even primary alcohols. In contrast to the representative Ti reagents, which were ineffective for this purpos
Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI
Liu, Chen,Liu, Yongjun,Qi, Yan,Song, Bin,Wang, Liang,Xiao, Shuhuan
supporting information, p. 6169 - 6172 (2021/06/30)
Grignard-type additions were readily achieved under the mediation of CuI (10 mol%) and samarium (2 equiv.) by employing various organohalides,e.g.benzyl, aryl, heterocyclic and aliphatic halides (Cl, Br or I), and diverse carbonyl compounds (e.g.carbonic esters, carboxylic esters, acid anhydrides, acyl chlorides, ketones, aldehydes, propylene epoxides and formamides) to afford alcohols, ketones and aldehydes, respectively, with high efficiency and chemoselectivity, in which the organosamarium intermediate might be involved.
Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
, p. 8738 - 8741 (2021/09/08)
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
A simple and efficient copper oxide-catalyzed Barbier-Grignard reaction of unactivated aryl or alkyl bromides with ester
Gao, Fei,Deng, Xiang-Jun,Tang, Yu,Tang, Jin-Peng,Yang, Jun,Zhang, Yuan-Ming
supporting information, p. 880 - 883 (2014/02/14)
An efficient one-pot route to synthesize tertiary alcohol compounds using Barbier-Grignard reaction of unactivated alkyl or aryl bromides with ester in THF at 65 C catalyzed by CuO has been developed and systematically investigated. A wide range of substituted tertiary alcohol compounds were obtained in good to high yields. The reaction is highly chemoselective. The mechanism involving the leaving group of R2O-group is discussed.
A simple and efficient copper oxide-catalyzed Barbier-Grignard reaction of unactivated aryl or alkyl bromides with ester
Gao, Fei,Deng, Xiang-Jun,Tang, Yu,Tang, Jin-Peng,Yang, Jun,Zhang, Yuan-Ming
supporting information, p. 880 - 883 (2015/03/03)
An efficient one-pot route to synthesize tertiary alcohol compounds using Barbier-Grignard reaction of unactivated alkyl or aryl bromides with ester in THF at 65 °C catalyzed by CuO has been developed and systematically investigated. A wide range of substituted tertiary alcohol compounds were obtained in good to high yields. The reaction is highly chemoselective. The mechanism involving the leaving group of R2O-group is discussed.
Modern Friedel-Crafts chemistry. Part-26. A facile synthesis of trans-2-methyl-1-phenylindan via rearranged intramolecular cyclialkylation of 1,2-diphenyl-2-methyl-2-propanol under Friedel-Crafts conditions
Khalaf, Ali A.,Albar, Hassan A.
, p. 518 - 521 (2007/10/03)
1,2-Diphenyl-2-methyl-2-propanol (1) was prepared by two alternative Grignard methods. Treatment of 1 with AlCl3, AlCl3/CH 3NO2 or K10 clay catalyst in benzene, toluene of dichloromethane solvent at varying temperatures for varying times gave trans-2-methyl-1-phenylindan (4) as sole or major product. Side products including isomeric alkenes 7 and 8, isomeric chlorides 9 and 10, isomeric triarylated isobutanes 11-14, 1-methyl-3-phenylindan (5) and 2-methyl-1-phenylindene (6) were also detected by GC-MS technique. Mechanistic interpretations and explanatory comments are offered.
Barbier/Grignard-type allylation or benzylation mediated by the mischmetall/SmI2(cat.) system
Di Scala, Aurore,Garbacia, Stefania,Helion, Florence,Lannou, Marie-Isabelle,Namy, Jean-Louis
, p. 2989 - 2995 (2007/10/03)
Barbier- and Grignard-type allylation and benzylation have been achieved by the use of samarium diiodide in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a coreductant. Plausible catalytic schemes are proposed. In addition, organocerium and -lanthanum reagents have been obtained from samarium diiodide catalysed reactions between organic halides and cerium or lanthanum metal, giving a new route to organolanthanoid compounds. It also appears that trivalent benzyl and allyl organometallic compounds of cerium and lanthanum are much more stable than the corresponding samarium ones. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Synthesis, structural characterization, and reactivity of zirconium complexes containing trimethylenemethane-based ligands
Rodriguez, George,Bazan, Guillermo C.
, p. 343 - 352 (2007/10/03)
General synthetic routes to zirconium metallocene-like complexes containing derivatives of the dianionic trimethylenemethane (TMM) ligand are presented. One approach consists of reacting the dilithium salts of TMM, tribenzylidenemethane (TBM), tert-butylt
Additions of Alkyllanthanum Triflates to Carbonyl Compounds: Reactive Organometallic Nucleophiles
Collins, Scott,Hong, Yaping,Hoover, Gordon J.,Veit, Jennifer R.
, p. 3565 - 3568 (2007/10/02)
Addition of alkyl- or aryllithium compounds to lanthanum(III) triflate in ethereal solvents produces the title reagents 2 that undergo nucleophilic addition to carbonyl compounds under mild conditions.These reagents resemble alkylcerium halides in their reactions with enolizable carbonyl compounds but are more reactive.In particular, they are useful for the conversion of hindered, tertiary amides to the ketones. 1H NMR spectroscopy was employed to clarify mechanistic aspects of this addition process.The title reagents actually appear to be a mixture of several species; formulation of their structure has proven elusive.However, in the presence of a tertiary amide, these species react to give a single, tetrahedral intermediate, which is quite stable in solution.
