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Pd@CeO 2 ‐catalyzed cyanation of aryl iodides with K 4 Fe(CN) 6 ·3H 2 O under visible light irradiation
Author(s) -
Wang Shengyu,
Wang Jianqiang,
Pan Junyi,
Liu Cheng,
Gong Xubin,
Guo Cheng
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6135
Subject(s) - cyanation , chemistry , aryl , catalysis , cyanide , visible spectrum , photocatalysis , reusability , irradiation , photochemistry , inorganic chemistry , organic chemistry , materials science , alkyl , physics , optoelectronics , software , computer science , nuclear physics , programming language
Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO 2 , nontoxic cyanide source K 4 [Fe (CN) 6 ]·3H 2 O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO 2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1‐iodo‐4‐nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO 2 ‐catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.