Synthesis 2023; 55(14): 2143-2150
DOI: 10.1055/a-2044-9651
paper

One-Pot, Metal-Free Synthesis of Phenols from Arylboronic Acids and Subsequent Conversion with N-Hydroxyphthalimide Esters

Zhigang Zhang
a   College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Di Ding
a   College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Yiming Yang
a   College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Ruiying Wan
b   Experimental Center, Shandong Provincial Key Laboratory of Traditional Chinese Medicine, Key Laboratory of Traditional Chinese Medicine Classical Theory, Ministry of Education, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Lili Gong
b   Experimental Center, Shandong Provincial Key Laboratory of Traditional Chinese Medicine, Key Laboratory of Traditional Chinese Medicine Classical Theory, Ministry of Education, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Haixing Guan
b   Experimental Center, Shandong Provincial Key Laboratory of Traditional Chinese Medicine, Key Laboratory of Traditional Chinese Medicine Classical Theory, Ministry of Education, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
,
Wei Li
a   College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, P. R. of China
› Author Affiliations
The authors acknowledge the National Key Research and Development Program of China (No. SQ2017YFC170600), Key R & D plan (major­ innovation project) project of Shandong Province (No. 2021CXGC010510), and Shandong University of Traditional Chinese Medicine (2022043, 2022050) for financial support.


Abstract

A one-pot synthesis of phenyl esters between N-hydroxyphthalimide (NHP) esters derived from carboxylic acid and arylboronic acids is developed. This tandem reaction underwent mild conditions with a broad range of substrates scope (up to 27 examples) in good to excellent yields (up to 93% yield). The reaction can be easily scaled up, which thus pave the way for further applications in late-stage modification.

Supporting Information



Publication History

Received: 15 December 2022

Accepted after revision: 01 March 2023

Accepted Manuscript online:
01 March 2023

Article published online:
03 April 2023

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