50735-91-6Relevant academic research and scientific papers
Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation
Zhu, Dianhu,Lv, Leiyang,Li, Chen-Chen,Ung, Sosthene,Gao, Jian,Li, Chao-Jun
supporting information, p. 16520 - 16524 (2018/11/23)
Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
Stereoselective synthesis of dienes from N-allylhydrazones
Mundal, Devon A.,Lutz, Kelly E.,Thomson, Regan J.
supporting information; experimental part, p. 465 - 468 (2009/07/11)
(Chemical Equation Presented) A new method for the stereoselective synthesis of dienes from aldehydes and N-allylhydrazine derivatives has been developed. High levels of (E)-stereoselectivity are obtained for a variety of substrates. Addition of a dienoph
