Issue 35, 2022

Regioselective transformation of 3-phosphoryl benzyne intermediates to diverse phosphorus-substituted arenes

Abstract

Herein, pre-functionalized benzyne precursors 5, 6 and 10 bearing a phosphoryl group were efficiently synthesized through a phospho-Fries rearrangement reaction on gram scales. Based on the versatile benzyne reactions ranging from nucleophilic addition and [3+2] and [4+2] cycloadditions to insertion reactions, a series of arylated organophosphorus molecules were readily achieved under mild reaction conditions. Attributed to the electron-withdrawing ability and the steric hindrance environment of phosphoryl groups, the reaction proceeded with high regioselectivity at the C1 position of 3-phosphoryl benzynes via a nucleophilic attack. Thus, this report illustrated novel phosphorus-functionalized benzynes and their regioselective formation of various poly-substituted organophosphorus arenes.

Graphical abstract: Regioselective transformation of 3-phosphoryl benzyne intermediates to diverse phosphorus-substituted arenes

Supplementary files

Article information

Article type
Paper
Submitted
22 Jul 2022
Accepted
10 Aug 2022
First published
24 Aug 2022

New J. Chem., 2022,46, 17049-17054

Regioselective transformation of 3-phosphoryl benzyne intermediates to diverse phosphorus-substituted arenes

J. Wang, Z. Li, G. You, L. Xu, P. Gao and B. Rao, New J. Chem., 2022, 46, 17049 DOI: 10.1039/D2NJ03638J

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