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Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri‐ and Tetrasubstituted Cyclobutanes
Author(s) -
Colomer Ignacio,
Coura Barcelos Rosimeire,
Donohoe Timothy J.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201511683
Subject(s) - hypervalent molecule , cyclobutanes , iodine , chemistry , catalysis , stereoselectivity , reagent , solvent , styrene , combinatorial chemistry , organic chemistry , polymer , cycloaddition , copolymer
Reported herein is that the use of catalytic quantities of hypervalent iodine reagents (phenyliodine diacetate or Dess–Martin periodinane) allows the rapid and stereoselective formation of cyclobutanes under very mild reaction conditions. The presence of a fluorinated solvent is essential for the success of these reactions which form unsymmetrical tri‐ and tetrasubstituted cyclobutanes through a heterodimerization process involving two different alkenes.