Asymmetric Synthesis of Diarylmethyl Sulfones by Palladium‐Catalyzed Enantioselective Benzylic Substitution: A Remarkable Effect of Water. Issue 25 (14th April 2018) - Najib, Atifah
Abstract: A Pd/( R )‐BINAP‐catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The reaction occurs in a dynamic kinetic asymmetric transformation (DYKAT) manner and thus provides convergent access to optically active benzylic sulfones from racemic secondary benzylic carbonates. Additionally, the addition of H2 O is found to be critical for high enantioselectivity. Abstract : Dynamic road to sulfones : A Pd/( R )‐BINAP‐catalyzed enantioselective benzylic sulfonation of diarylmethyl carbonates with sodium sulfinates proceeds in a dynamic kinetic asymmetric transformation (DYKAT) to deliver the corresponding chiral diarylmethyl sulfones in good yields with high enantioselectivity. The key to success is the addition of H2 O as well as a judicious choice of chiral ancillary ligand.