Ligand coupling from hypervalent sulfur compounds, sulfuranes, allows the construction of carbon–carbon linkages between two organic fragments without using transition metal catalysts. Although pioneering studies on sulfurane-mediated ligand coupling demonstrated numerous carbon–carbon bond-forming (cross-)coupling reactions, this chemistry has been largely overlooked in organic synthesis over the past decades. I herein propose a research program to address unexplored aspects of sulfurane chemistry, namely modular synthesis of chiral sulfoxides, iterative synthesis of oligoheteroarenes, and expansion of substrate scope utilizing eta(6)-arene complexes. The outcome of my research will be important steps to establish a synthetic platform for sustainable, environmentally benign cross-couplings without relying on transition metals.
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