Organophosphorus compounds have received a lot of attention in recent decades due to their wide range of applications in industry as well as pharmacology and agriculture. Their unique properties and reactivity make them strong supporting ligands in catalysis. The cross coupling of aryl boronic acids with P(V)-H reagents has been demonstrated to be an effective method in forming P-C bonds; however, aryl boronic acids are typically more difficult to work with than their corresponding boronate esters, and the field of organoboron chemistry has recently been focused on incorporating boronate esters into organic compounds. A direct method to couple P(V)-H reagents with organoboronate esters was desired to expand the scope of organophosphorus reagents that could be achieved. Using the known conditions for P-C cross couplings with boronic acids a variety of alternative pre-catalysts, bases and solvents have been examined. Conditions to achieve the coupling of diethyl phosphite with aryl boronate esters has been achieved in good yields using copper-catalyzed conditions. The role of the base was found to be critical for the transformation, likely due to the need to deprotonate the diethyl phosphite and activate the boronate ester. The scope and limitations of the reaction will be discussed.

Direct C-P cross coupling of aryl boronate esters with dialkyl phosphites

ACS Spring 2022

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