Two recent applications of the cross-coupling reactions of organosulfur compounds will be discussed. The first one describes the application of this chemistry in the synthesis of highly-functionalyzed cyclobutenediones. Thioarylsubstituted cyclobutenedione 1 reacts with either organostannanes or boronic acids in the presence of Pd(0) and CuTC to give symmetric cyclobutenediones. Likewise, chlorothiophenylcyclobutenedione 2 was functionalized via a sequential cross-coupling with organostannanes at the Cl-bearing C atom and then at the S-bearing C atom with boronic acids to give non-symmetric cyclobutenediones. The second applications describes how 8-thiomethylbodipy 3 reacted smoothly with either boronic acids or organostannanes to give a family of meso-substituted Bodipy derivatives in yields that range from 65% to quantitative.