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Addition of Nucleophiles to Fluorinated Michael Acceptors
Author(s) -
Ramb Daniel C.,
Lerchen Andreas,
Kischkewitz Marvin,
Beutel Bernd,
Fustero Santos,
Haufe Günter
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600088
Subject(s) - nitromethane , nucleophile , chemistry , michael reaction , diethyl malonate , yield (engineering) , primary (astronomy) , organic chemistry , substrate (aquarium) , malonate , medicinal chemistry , catalysis , materials science , physics , oceanography , astronomy , metallurgy , geology
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.