Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri- and Tetrasubstituted Cyclobutanes

Ignacio Colomer; Rosimeire Coura Barcelos; Timothy J Donohoe

doi:10.1002/anie.201511683

Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri- and Tetrasubstituted Cyclobutanes

Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4748-52. doi: 10.1002/anie.201511683. Epub 2016 Mar 7.

Authors

Ignacio Colomer¹, Rosimeire Coura Barcelos¹, Timothy J Donohoe²

Affiliations

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
² Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk.

PMID: 26948413
DOI: 10.1002/anie.201511683

Abstract

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.

Keywords: cyclizations; dimerization; hypervalent compounds; small ring systems; total synthesis.

Publication types

Research Support, Non-U.S. Gov't