7779-78-4Relevant 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
, 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.
Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols
Donabauer, Karsten,Maity, Mitasree,Berger, Anna Lucia,Huff, Gregory S.,Crespi, Stefano,K?nig, Burkhard
, p. 5162 - 5166 (2019/06/05)
We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.
Le benzyltrimethylsilane, un agent pratique de benzylation
Bennetau, Bernard,Bordeau, Michel,Dunogues, Jacques
, p. 90 - 93 (2007/10/02)
In the presence of Bu4N(1+))*F(1-), benzyltrimethylsilane behaves as a convenient benzylation reagent.In the reaction with non conjugated aldehydes, pehenethylalcohols are obtained in satisfactory yields upon hydrolysis, while the formation of bibenzyl or ortho products are not observed.When the reaction occurs with α,β-unsaturated aldehydes and ketones, only 1,2-addition is observed even in the case of chalcone.