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Photocatalytic alkoxylation of benzene with 3-cyano-1-methylquinolinium ion

Kei Ohkubo, Takaki Kobayashi, and Shunichi Fukuzumi

Open Access Open Access

Abstract

One-pot alkoxylation of benzene with alcohols occurs under photoirradiation of 3-cyano-1-methylquinolinium ion in an oxygen-saturated acetonitrile solution containing benzene and alcohols. The photocatalytic reaction mechanism was clarified by nanosecond laser flash photolysis. The photocataytic alkoxylation of benzene is initiated by photoinduced electron transfer from benzene to the singlet excited state of 3-cyano-1-methylquinolinium ion, followed by the nucleophilic addition of alcohols to benzene radical cation. In the case of photoethoxylation, the optimal product and quantum yields of ethoxybenzene were 20% and 10%, respectively.

©2012 Optical Society of America

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Figures (7)
Fig. 1
Fig. 1 Stoichiometric equation of photoalkoxylation of benzene with alcohol by QuCN+.

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Fig. 2
Fig. 2 Time profiles of consumption of benzene (blue) and formation of alkoxybenzene (red) in the photocatalytic alkoxylation of benzene with (a) methanol, (b) ethanol, (c) iso-propanol and (d) tert-butanol catalyzed by QuCN+ in oxygen-saturated MeCN (1.0 mL) at 298 K.

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Fig. 3
Fig. 3 Quantum yield of formation of ethoxybenzene (Φ) vs. [EtOH].

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Fig. 4
Fig. 4 (a) Fluorescence spectra of QuCN+ (20 μM) with various concentrations of benzene (0 – 4.0 mM) in deaerated MeCN excited at 330 nm. (b) Stern-Volmer plot for the fluorescence quenching of 1QuCN+* by benzene.

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Fig. 5
Fig. 5 (a) Transient absorption spectrum of an MeCN solution of QuCN+ and benzene (1.0 M) taken at 1 μs after nanosecond laser excitation (λex = 355 nm). (b) Decay time profiles of absorbance at 850 nm with various concentrations of MeOH (0 – 42 mM). (c) Plots of decay rate constants vs. concentration of alcohols.

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Fig. 6
Fig. 6 Photocatalytic mechanism of alkoxylation of benzene with QuCN+.

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Fig. 7
Fig. 7 Stoichiometric equation of photocyclization of 3-phenyl-1-propanol by QuCN+.

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Tables (1)

Tables Icon

Table 1 Conversions, selectivities, yields, and quantum yields (Φ) of photocatalytic alkoxylation of benzene with alcohols in MeCN[a]

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