Nucleophilic substitution of hydrogen in nitroarenes, S_NArH, proceeds via fast addition of nucleophiles at positions occupied by hydrogen to form σ^H adducts that are subsequently converted into products of substitution of hydrogen on a few ways. It should be stressed that S_NArH proceeds much faster than conventional nucleophilic substitution of halogens, S_NAr. 

Facile introduction a variety of functionalized carbon substituents into nitroaromatic rings via S_NArH with carbanions opens wide possibilities for synthesis of indoles as exemplified in scheme

In the lecture will be presented basic variants of nucleophilic substitution of hydrogen, main methods of synthesis of indolesvia S_NArH and examples of application of these methods.

References:

1.   M. Mąkosza, Chem. Soc. Rev., 2010, 39, 2855; Synthesis, 2011, 2341.

2.   M. Mąkosza, K. Wojciechowski, Chem. Rev., 2004, 104, 2631.

3.   M. Mąkosza, K. Wojciechowski, Heterocycles, 2014, 88, 75.

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