79098-20-7Relevant articles and documents
Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling
Dupuy, Stéphanie,Zhang, Ke-Feng,Goutierre, Anne-Sophie,Baudoin, Olivier
, p. 14793 - 14797 (2016/11/23)
Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C?H bond functionalization methods. We describe herein a new step-economical approach that enables C?C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
New One-pot Cross-coupling Reaction between Grignard Reagents and Alkoxymethyldiphenylphosphonium Iodides in situ-Formed from Alcohols, Chlorodiphenylphosphine and Iodomethane
Shintou, Taichi,Kikuchi, Wataru,Mukaiyama, Teruaki
, p. 676 - 677 (2007/10/03)
A new one-pot cross-coupling reaction between Grignard reagents and alkoxymethyldiphenylphosphonium iodides, which were in situ-formed from nBuLi-treated alcohols, chlorodiphenylphosphine and iodomethane, proceeded smoothly to afford the corresponding coupling products in good to high yields.
Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini,Kelley, Shane W.
, p. 3688 - 3695 (2007/10/03)
(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.