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Publications, such as the following example from Journal of the American Chemical Society, will be highlighted as outlined below with a short form version of the abstract, the graphical abstract and a handy clickable button that takes you straight to the paper!

Journal of the American Chemical Society

Difunctionalization of C–C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins

S. H. Bennett, A. Fawcett, E. H. Denton, T. Biberger, V. Fasano, N. Winter & V. K. Aggarwal*

J. Am. Chem. Soc. 2020, 142, 16766–16775 (DOI: 10.1021/jacs.0c07357).

Difunctionalization reactions of C–C σ-bonds have the potential to streamline access to molecules that would otherwise be difficult to prepare. However, the development of such reactions is challenging because C–C σ-bonds are typically unreactive. Exploiting the high ring-strain energy of polycyclic carbocycles is a common strategy to weaken and facilitate the reaction of C–C σ-bonds, but there are limited examples of highly strained C–C σ-bonds being used in difunctionalization reactions. The authors demonstrate that highly strained bicyclo[1.1.0]butyl (BCB) boronate complexes (strain energy ca. 65 kcal/mol), which were prepared by reacting boronic esters with BCB lithium, react with electrophiles to achieve the diastereoselective difunctionalization of the strained central C–C σ-bond of the BCB unit. The reaction shows broad substrate scope, with a range of different electrophiles and boronic esters being successfully employed to form a diverse set of 1,1,3-trisubstituted cyclobutanes (>50 examples) with high diastereoselectivity.

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