Andrei Rogoza
The only (non-diazonium) example was found in transformation
6-methoxy-1-naphthylamine + NaHSO3; +NaOH -> 6-methoxy-1-naphthol
J. Am. Chem. Soc., 1961, 83 (24), pp 5015–5019
DOI: 10.1021/ja01485a031
Triflation to Ar-N(SO2CF3)2 or transformation in N,N'-aryl(alkyl)imidazolium salt may be also is a solution for N-umpolung
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Andrei Rogoza
@Michael: thanks for valuable add-on. My answer was updated. If you have examples to demonstrate, please do not hide them from us
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Andrei Rogoza
Yes, sure, Sandip, thanks for reminder!
Bucherer, H. Th. (1904), Über die Einwirkung schwefligsaurer Salze auf aromatische Amido- und Hydroxylverbindungen. J. Prakt. Chem., 69: 49–91. doi: 10.1002/prac.19040690105
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