Development of meta-C-H functionalization reactions at room temperature continues to be a tough challenge. Use of a phosphonate linkage allowed a Pd (II) catalyzed meta-C-H functionalization at room temperature while incorporating a cyanophenol-based directing moiety. Successful implementation of sequential di-meta-olefination led to the synthesis of a trialkenyl arene, which has applications in organic electronics and optoelectronics. Under robust conditions, C-O bond formation has been discovered for the meta hydroxylation and meta-acetoxylation.