Marczenko Katherine M, Zurakowski Joseph A, Bamford Karlee L, MacMillan Joshua W M, Chitnis Saurabh S
Chemistry Department, Dalhousie University, 6274 Coburg Road, Halifax, Nova Scotia, Canada.
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada.
Angew Chem Int Ed Engl. 2019 Dec 9;58(50):18096-18101. doi: 10.1002/anie.201911842. Epub 2019 Oct 24.
A rigid naphthalenediamine framework has been used to prepare antimony hydrides that feature LUMO shapes and energies similar to those found in secondary boranes. By exploiting this feature, we introduce the first examples of uncatalyzed hydrostibination reactions of robust C≡C, C=C, C=O, and N=N bonds as new elementary hydrometalation reactions analogous to hydroboration. These results endorse the notion of a diagonal relationship between the lightest p-block element and the heaviest Group 15 elements and may lead to the conception of novel reaction chemistry.
