The First Boron-Tethered Radical Cyclizations and Intramolecular Homolytic Substitutions at Boron

Robert A Batey; David V Smil

doi:10.1002/(SICI)1521-3773(19990614)38:12<1798::AID-ANIE1798>3.0.CO;2-0

The First Boron-Tethered Radical Cyclizations and Intramolecular Homolytic Substitutions at Boron

Angew Chem Int Ed Engl. 1999 Jun 14;38(12):1798-1800. doi: 10.1002/(SICI)1521-3773(19990614)38:12<1798::AID-ANIE1798>3.0.CO;2-0.

Authors

Robert A Batey¹, David V Smil¹

Affiliation

¹ Department of Chemistry, Lash Miller Laboratories, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 (Canada), Fax: (+1) 416-978-5059.

Abstract

5-, 6-, and even 7-exo-trig radical cyclizations (1→2) are possible by applying a new boron-tethering approach with alkenylboronic esters. For certain substitution patterns, a subsequent intramolecular homolytic substitution (S_H i) reaction at boron occurs (2→3) and leads to rearranged products. The C-B bond of the intermediate boracycles is readily oxidized to give diol products.

Keywords: Boron; Cyclizations; Radical reactions; Rearrangements.