Much attention has been paid for the cleavage reactions of unactivated C-H bond because of potential utilization for the first elementary step of molecular transformation. The formation of carbon-heteroatom bonds by reductive elimination is less common and elimination reactions that form C-O, C-N and C-S bonds has been instrumental in developing practical routes to aromatic amines, ethers and ... [Show full abstract] sulfides but yet has been observed directly. Therefore, the research has focused on the molecular transformation of ortho substituted phenol derivatives of 2, 6-xylenol for sp<SUP>3</SUP> C-H bond cleavage reaction of the ortho methyl group. One of possible scheme is depicted in this study that describes (1) Insertion reaction and (2) Reductive elimination to give benzopyran derivatives. The insertion of Dimethyl acetylenedicarboxylate (DMAD) into ruthenacyle complex gives intermediate complexes. Treatment on both complexes with I<SUB>2</SUB> as an oxidant produces reductive elimination products. Molecular transformation of 2, 6-xylenol to benzopyran derivatives via C-H bond cleavage by ruthenium complex is carried out by combination of these elemental reactions.