923-28-4Relevant articles and documents
C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis
Murugesan, Vetrivelan,Ganguly, Anirban,Karthika, Ardra,Rasappan, Ramesh
supporting information, p. 5389 - 5393 (2021/07/21)
Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.
A Ruthenium-Grafted Hydrotalcite as a Multifunctional Catalyst for Direct α-Alkylation of Nitriles with Primary Alcohols
Motokura, Ken,Nishimura, Daisuke,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 5662 - 5663 (2007/10/03)
Treatment of a hydrotacite, Mg6Al2(OH)16CO3, with an aqueous solution of RuCl3·nH2O afforded a monomeric Ru(IV) species on the surface of the hydrotalcite. This novel Ru-grafted hydrotalcite (Ru/HT) efficiently catalyzed α-alkylation of nitriles with primary alcohols through the cooperative catalysis between the Ru species and the surface base sites. The catalyst system could be further extended for the one-pot synthesis of α,α-dialkylated phenylacetonitriles via the base-catalyzed Michael reaction of α-alkylated phenylacetonitrile with activate olefins. Copyright
Development of new iron catalysts for the tandem isomerization-aldol condensation of allylic alcohols
Uma, Ramalinga,Gouault, Nicolas,Crévisy, Christophe,Grée, René
, p. 6187 - 6190 (2007/10/03)
(bda)Fe(CO)3 and (COT)Fe(CO)3 are shown to be excellent catalysts for the tandem isomerization-aldol reaction of allylic alcohols with aldehydes and to significantly increase the scope of this aldolization process, especially, in the