Addition of Nucleophiles to Fluorinated Michael Acceptors. Issue 9 (14th March 2016)

• Record Type: Journal Article
• Authors: Ramb, Daniel C.; Lerchen, Andreas; Kischkewitz, Marvin; Beutel, Bernd; Fustero, Santos; Haufe, Günter
• Is Part Of: European journal of organic chemistry. Issue 9(2016)
• Page Start: 1751
• Page End: 1759
• Publication Date: 2016-03-14
• Subjects: Fluorine -- Enones -- Michael addition -- Nucleophilic addition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600088
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A series of nucleophiles, including primary and secondary amines, primary alcohols, and thiols, as well as diethyl malonate and nitromethane, were added to different fluorinated Michael acceptors including 2‐fluoroalk‐1‐en‐3‐ones and 2‐fluoro‐1‐phenylprop‐2‐en‐1‐one. The resulting β‐substituted α‐fluoro ketones were isolated in 34–92 % yield, depending on the substrate and the nucleophile. The best yields were obtained with secondary amines and with p ‐methylthiophenol. Abstract : Carbon, nitrogen, sulfur, and oxygen nucleophiles were added to fluorinated Michael acceptors such as 2‐fluoroalk‐1‐en‐3‐ones and 2‐fluoro‐1‐phenylprop‐2‐en‐1‐one to give the target Michael adducts in 32–92 % yield.