Nathan D. Schley

The aim of the Schley research group is the application of organometallic chemistry to unmask latent reactivity in organic substrates. Oxidation of simple hydrocarbons provides functional groups which serve as handles for further transformations, but methods for selective oxidation of C-H bonds are limited. Our goal is to meet the challenge of enabling new oxidative, catalytic transformations of C-H bonds by making use of unconventional activation strategies. Our research is guided by exploratory stoichiometric chemistry, kinetic analyses, and thoughtful mechanistic studies. A major aim of our research program is in developing catalysts for the borylation of C-H bonds, particularly the borylation of aliphatic sp3 C-H bonds to their corresponding alkylboronate esters. Our program also explores catalyst development through the identification of new, functional ligand platforms. For instance, our alkane borylation catalysts incorporate versatile dipyridylarylmethane ligand derivatives. Separately, we are developing the [1.1.1]propellane-derived bicyclo[1.1.1]pentyl group as a phosphine substituent including in the synthesis of tris(bicyclo[1.1.1]pentyl)phosphine, the smallest tri-tert-alkyl phosphine yet prepared. Our ongoing work is expanding this exciting new dimension in organophosphorus chemistry to the preparation and study of bis(bicyclopentyl)phosphine variants of privileged ligand classes.

Perry, G. L.; Schley, N. D., "Tris(bicyclo[1.1.1]pentyl)phosphine: An Exceptionally Small Tri-tert-alkylphosphine and Its Bis-Ligated Pd(0) Complex" J. Am. Chem. Soc., 2023, 145, 7005–7010.