One-pot alpha-ferrocenylalkylation of amines and alcohols with alpha-ferrocenyl substituted alcohols under acid-free conditions

摘要

One-pot reaction of FcCH(R)OH with equimolar quantities of (BuLi)-Li-n and EtOCOCl followed by an excess of amine produces N-(alpha-ferrocenylalkyl)amines in up to 98% yields. Nitrogen heteroaryl amines undergo the alpha-ferrocenylalkylation at the amino group. The alpha-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 alpha-ferrocenylalkyl carbonates FcCH(R)OCOOEt. The side reactions associated with this protocol are discussed. (C) 2018 Elsevier B.V. All rights reserved.