Issue 33, 2021

Synthesis of non-C2 symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts

Abstract

We developed herein a regioselective construction of non-C2 symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts under mild conditions. The employment of copper salt could inhibit the further O-arylation of the newly formed biaryl products, otherwise, O-arylated NOBIN-type products were furnished in moderate to good isolated yields. The products of this protocol can be further converted into highly valuable functional molecules and heterocycles.

Graphical abstract: Synthesis of non-C2 symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts

Supplementary files

Article information

Article type
Paper
Submitted
02 Apr 2021
Accepted
05 Aug 2021
First published
05 Aug 2021

Org. Biomol. Chem., 2021,19, 7246-7251

Synthesis of non-C2 symmetrical NOBIN-type biaryls through a cascade N-arylation and [3,3]-sigmatropic rearrangement from O-arylhydroxylamines and diaryliodonium salts

F. Liu, M. Wang, J. Qu, H. Lu and H. Gao, Org. Biomol. Chem., 2021, 19, 7246 DOI: 10.1039/D1OB00636C

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