Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones

Diarylmethanes and diarylketones are important chemicals which feature in various materials and bioactive molecules; however, efficient divergent strategies for their synthesis are lacking. Now, in this study, we present an efficient and versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones using only aldehydes and arenes as starting materials. This was successfully achieved through: (1) Regioselective Ar-H alkylation to synthesize benzhydryl-phosphonium salts via one-pot, four-component coupling reactions that utilize simple, commercially available reagents. (2) We demonstrated the utility of these phosphonium salt building blocks through chemoselective reductions or oxidations of the benzylic C–P bond, leading to unsymmetrical diarylmethanes and diarylketones, respectively. Notably, the reduction process enables the synthesis of fully deuterated benzylic diarylmethanes by utilizing D2O as a deuterium source. The products obtained serve as valuable building blocks and are produced in high yields. This new approach is straightforward, featuring simple setups that promise to facilitate novel transformations for applications in both academic and pharmaceutical research.