3964-66-7Relevant academic research and scientific papers
Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
Neate, Peter G.N.,Zhang, Bufan,Conforti, Jessica,Brennessel, William W.,Neidig, Michael L.
supporting information, p. 5958 - 5963 (2021/08/18)
Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.
Catalytic hydrogen atom transfer (HAT) for sustainable and diastereoselective radical reduction
Gansaeuer, Andreas,Klatte, Max,Braendle, Gerhard M.,Friedrich, Joachim
supporting information; experimental part, p. 8891 - 8894 (2012/10/08)
Going cyclic! A catalytic cycle and cyclic transition states enable a novel sustainable and catalytic hydrogen atom transfer (HAT) for highly diastereoselective radical reductions. Readily available nontoxic silanes are the terminal reductants for epoxides that are opened by bifunctional titanocene(III) hydride catalysts. Copyright
Selective catalytic C-H alkylation of alkenes with alcohols
Lee, Dong-Hwan,Kwon, Ki-Hyeok,Yi, Chae S.
scheme or table, p. 1613 - 1616 (2012/02/01)
Alkenes and alcohols are among the most abundant and commonly used organic feedstock in industrial processes. We report a selective catalytic alkylation reaction of alkenes with alcohols that forms a carbon-carbon bond between vinyl carbon-hydrogen (C-H) and carbon-hydroxy centers with the concomitant loss of water. The cationic ruthenium complex [(C6H6)(PCy 3)(CO)RuH]+BF4- (Cy, cyclohexyl) catalyzes the alkylation in solution within 2 to 8 hours at temperatures ranging from 75° to 110°C and tolerates a broad range of substrate functionality, including amines and carbonyls. Preliminary mechanistic studies are inconsistent with Friedel-Crafts-type electrophilic activation of the alcohols, suggesting instead a vinyl C-H activation pathway with opposite electronic polarization.
Synthesis of biologically active substances based on phenoxyethanol derivatives
Kukovinets,Yamansarova,Kasradze,Lozhkina,Zainullin,Abdullin
, p. 673 - 677 (2007/10/03)
By reaction of phenoxyethanol with diverse structure acyl chlorides phenoxyethanol esters were synthesized containing in the molecule fragments of undecene acid and also of some ketocarboxylic acids. The latter acids were obtained by ozonation of alkylcyclenes. 2005 Pleiades Publishing, Inc.
Total synthesis of (+)-myriocin and (-)-sphingofungin E from aldohexoses using overman rearrangement as the key reaction
Oishi, Takeshi,Ando, Koji,Inomiya, Kenjin,Sato, Hideyuki,Iida, Masatoshi,Chida, Noritaka
, p. 1927 - 1947 (2007/10/03)
Total synthesis starting from aldohexoses of naturally occurring α-substituted α-amino acids, (+)-myriocin (1) and (-)-sphingofungin E (2), is described. Overman rearrangement of allylic trichloroacetimidate 6E derived from D-mannose effectively generated the tetrasubstituted carbon with nitrogen, and subsequent Wittig olefination afforded the highly functionalized moiety 3 of myriocin stereoselectively. Sulfone-mediated coupling reaction of the allyl bromide 3 with C12 hydrophobic part 4 successfully constructed the carbon framework possessing E-olefin 28. Removal of the sulfone and protecting groups completed the chiral and stereoselective total synthesis of (+)-myriocin (1). A similar transformation starting from D-glucose also accomplished the total synthesis of (-)-sphingofungin E (2).
