One-pot α-ferrocenylalkylation of amines and alcohols with α-ferrocenyl substituted alcohols under neutral conditions

Publication date: Available online 28 October 2018Source: Journal of Organometallic ChemistryAuthor(s): Ekaterina V. Shevaldina, Anastasia D. Shagina, Andrey B. Ponomaryov, Sergey K. MoiseevAbstractOne-pot reaction of FcCH(R)OH with equimolar quantities of BunLi and EtOCOCl followed by an excess of amine produces N-(α-ferrocenylalkyl)amines in up to 98% yields. Nitrogen heteroaryl amines undergo the α-ferrocenylalkylation at the amino group. The α-ferrocenylalkylation of alcohols and phenols (R’OH) leads to a formation of ethers FcCH(R)OR′ in lower yields. The reactions proceed via an intermediate formation of α-ferrocenylalkyl carbonates FcCH(R)OCOOEt. The side reactions associated with this protocol are discussed.Graphical abstract

Source: Journal of Organometallic Chemistry - October 29, 2018 Category: Chemistry Source Type: research