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The first hydrogenation step of benzene, which is endergonic in the electronic ground state (S 0 ), becomes exergonic in the first triplet state (T 1 ). This is in line with Baird's rule, which tells that benzene is antiaromatic and destabilized in its T 1  state and also in its first singlet excited state (S 1 ), opposite to S 0 , where it is aromatic and remarkably unreactive. Here we utilized this feature to show that benzene and several polycyclic aromatic hydrocarbons (PAHs) to various extents undergo metal-free photochemical (hydro)silylations and transfer-hydrogenations at mild conditions, with the highest yield for naphthalene (photosilylation: 21%). Quantum chemical computations reveal that T 1 -state benzene is excellent at H-atom abstraction, while cyclooctatetraene, aromatic in the T 1  and S 1  states according to Baird's rule, is unreactive. Remarkably, also CVD-graphene on SiO 2  is efficiently transfer-photohydrogenated using formic acid/water mixtures together with white light or solar irradiation under metal-free conditions.

Metal-free photochemical silylations and transfer hydrogenations of benzenoid hydrocarbons and graphene