Bismuth Compounds in Radical Catalysis: Transition Metal Bismuthanes Facilitate Thermally Induced Cycloisomerizations.

Author(s) Ramler, J.; Krummenacher, I.; Lichtenberg, C.
Journal Angew Chem Int Ed Engl
Date Published 2019 Sep 09
Abstract

The controlled radical chemistry of bismuth compounds is still in its infancy. Further developments are fueled by the properties of these complexes (e.g., low toxicity, high functional group tolerance, low homolytic bond dissociation energies, and reversible homolytic bond dissociations), which are highly attractive for applications in synthetic chemistry. Here we report the first catalytic application of transition metal bismuthanes (i.e. compounds with a Bi-TM bond; TM=transition metal). Using the catalyzed radical cyclo-isomerization of δ-iodo-olefins as a model reaction, characteristics complementary or superior to known B, Mn, Cu, Zn, Sn, and alkali metal reagents are demonstrated (including a different crucial intermediate), establishing transition metal bismuthanes as a new class of (pre-)catalysts for controlled radical reactions.

DOI 10.1002/anie.201904365
ISSN 1521-3773
Citation Ramler J, Krummenacher I, Lichtenberg C. Bismuth Compounds in Radical Catalysis: Transition Metal Bismuthanes Facilitate Thermally Induced Cycloisomerizations. Angew Chem Int Ed Engl. 2019;58(37):12924-12929.