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Furyl‐Substituted Mixed Phosphonium–Iodonium Ylides in the Synthesis of Annelated P‐Containing Heterocyclic Compounds
Author(s) -
Matveeva Elena D.,
Vinogradov Dmitrii S.,
Podrugina Tatyana A.,
Nekipelova Tatiana D.,
Mironov Andrey V.,
Gleiter Rolf,
Zefirov Nikolay S.
Publication year - 2015
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.201500876
Subject(s) - phosphonium , chemistry , furan , electrophile , ring (chemistry) , ylide , medicinal chemistry , organic chemistry , stereochemistry , catalysis
Photochemical reactions between stabilized furyl‐substituted phosphonium–iodonium ylides and terminal acetylenes led to the formation of new P‐containing heterocyclic compounds. For the heterocyclization of 2‐furyl‐substituted ylides, we observed an unprecedented electrophilic ipso attack onto the α position of the furan ring in a carbocationic intermediate, leading – via a spiro intermediate – to the rearranged product with a 2,3‐shift in the furan ring.