Regiodivergent Aromatic Electrophilic Substitution Using Nitrosoarenes in Hexafluoroisopropanol: A Gateway for Diarylamines and  p ‐Iminoquinones Synthesis | Zendy

Pradhan Suman | Zendy; Roy Sourav | Zendy; Ghosh Soumen | Zendy; Chatterjee Indranil | Zendy

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Regiodivergent Aromatic Electrophilic Substitution Using Nitrosoarenes in Hexafluoroisopropanol: A Gateway for Diarylamines and p ‐Iminoquinones Synthesis

Author(s) -

Pradhan Suman,

Roy Sourav,

Ghosh Soumen,

Chatterjee Indranil

Publication year - 2019

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201900788

Subject(s) - chemistry , electrophile , electrophilic amination , amination , electrophilic aromatic substitution , medicinal chemistry , combinatorial chemistry , domino , electrophilic substitution , reagent , organic chemistry , catalysis

A metal‐free aromatic electrophilic substitution reaction using nitrosoarenes as the electrophile in 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) is reported. HFIP activates nitrosoarene towards the electrophilic C−H amination followed by a concomitant N−O bond cleavage to deliver diarylamines without requiring any extra reagent or further treatment. The dual electrophilic nature of nitrosoarene permits a switchover of selectivity to C−H oxygenation furnishing dearomatized p ‐iminoquinones following a unique mechanistic rationale of two consecutive [2,3] sigmatropic rearrangement in nitroso‐chemistry.

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