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Fluorinated Alkynylphosphonates in C , C ‐Cyclizations: Regioselective Formation of Polysubstituted Fluorinated Arylphosphonates
Author(s) -
Duda Blazej,
Tverdomed Sergey N.,
Ionin Boris I.,
Röschenthaler GerdVolker
Publication year - 2014
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.201402188
Subject(s) - regioselectivity , chemistry , phosphoramidate , yield (engineering) , phosphonate , medicinal chemistry , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
Abstract The regioselective C , C ‐cyclization of selected 1,4‐bipolar substrates with fluorinated alkynylphosphonates provided polysubstituted benzenes and naphthalenes in up to 98 % yield. For the case in which tetraethyl ethynylbisphosphonate was used, an unexpected phosphonate–phosphoramidate rearrangement was, for the first time, observed, which occurred in excellent yield.