Issue 9, 2020

Transition-metal-free aerobic C–O bond formation via C–N bond cleavage

Abstract

Herein, we disclosed a transition metal-free cascade protocol for the construction of 2-hydroxy-2′-amino-1,1′-biaryls that are difficult to prepare by employing conventional methods. The nucleophilic substitution of arylhydroxylamines to arylammonium salts at room temperature generates transient N,O-diarylhydroxylamines that could rapidly undergo a tandem process, including a [3,3]-sigmatropic rearrangement and rearomatization to afford NOBIN analogues.

Graphical abstract: Transition-metal-free aerobic C–O bond formation via C–N bond cleavage

Supplementary files

Article information

Article type
Research Article
Submitted
10 Feb 2020
Accepted
22 Mar 2020
First published
30 Mar 2020

Org. Chem. Front., 2020,7, 1077-1081

Transition-metal-free aerobic C–O bond formation via C–N bond cleavage

L. Guo, F. Liu, L. Wang, H. Yuan, L. Feng, H. Lu and H. Gao, Org. Chem. Front., 2020, 7, 1077 DOI: 10.1039/D0QO00173B

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