Visible-light-induced direct C-H alkylation of polycyclic aromatic hydrocarbons with alkylsulfones
Motoo Ohtsuka1, Koushik Ghosh1, Jacky C-H Yim1
1Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University Chikusa Nagoya Aichi 464-8601 Japan cruddenc@chem.queensu.ca nambo.masakazu.p3@f.mail.nagoya-u.ac.jp.
Abstract:
Polycyclic aromatic hydrocarbons (PAHs) are fragments of graphene that have attracted considerable attention as a new class of carbon-based materials. The functionalization of edge positions in PAHs is important to enable the modulation of physical and chemical properties essential for various applications. However, straightforward methods that combine functional group tolerance and regioselectivity remain sought after. Here we report a photochemical approach for the direct alkylation of carbon-hydrogen bonds in PAHs that takes place in a regiospecific manner, an outcome that has never been achieved in related thermal reactions. A reaction mechanism involving a single electron transfer process from photo-excited PAHs to sulfones, and a rationale for the origin of regioselectivity are proposed on the basis of spectroscopic analyses and theoretical calculations.
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