Radical-nucleophilic aromatic substitution or SRN1 in organic chemistry is a type of substitution reaction in which a certain substituent on an aromatic compound is replaced by a nucleophile through an intermediary free radical species:
The substituent X is a halide and nucleophiles can be sodium amide, an alkoxide or a carbon nucleophile such as an enolate.[1] In contrast to regular nucleophilic aromatic substitution, deactivating groups on the arene are not required.[2]
This reaction type was discovered in 1970 by Bunnett and Kim[3] and the abbreviation SRN1 stands for substitution radical-nucleophilic unimolecular as it shares properties with an aliphatic SN1 reaction. An example of this reaction type is the Sandmeyer reaction.
- ^ Phenomenon of radical anion fragmentation in the course of aromatic SRN reactions Roberto A. Rossi Acc. Chem. Res.; 1982; 15(6) pp 164 – 170; doi:10.1021/ar00078a001.
- ^ Rossi, R. A.; Pierini, A. B.; Santiago, A. N. Org. React. 1999, 54, 1. doi:10.1002/0471264180.or054.01
- ^ Evidence for a radical mechanism of aromatic "nucleophilic" substitution Joseph F. Bunnett and Jhong Kook Kim J. Am. Chem. Soc.; 1970; 92(25) pp 7463 – 7464. (doi:10.1021/ja00728a037)