Issue 8, 2021

Dearomative 1,6-addition of P(O)–H to in situ formed p-QM-like ion pairs from 2-benzofuryl-ols to C3-phosphinoyl hydrobenzofurans

Abstract

A dearomative C3-phosphorylation of 2-benzofuryl-ols with the P(O)–H species to C3-phosphinoyl hydrobenzofurans has been established. The key to achieve the high C3-regioselectivity is the use of an “OMe” group at the C6-position to enable the dearomative 1,6-addition of P(O)–H compounds to para-quinone methide (p-QM)-like ion pairs generated in situ from 2-benzofuran-ols. A “one-pot” tandem C3-phosphorylation/aromatization to C3-phosphinoyl benzofurans is also developed. This protocol not only provides an alternative method for the synthesis of C3-phosphinoyl hydrobenzofurans and benzofurans but also represents a new strategy for the dearomatization of benzofurans.

Graphical abstract: Dearomative 1,6-addition of P(O)–H to in situ formed p-QM-like ion pairs from 2-benzofuryl-ols to C3-phosphinoyl hydrobenzofurans

Supplementary files

Article information

Article type
Research Article
Submitted
15 yan 2021
Accepted
11 fev 2021
First published
18 fev 2021

Org. Chem. Front., 2021,8, 1756-1763

Dearomative 1,6-addition of P(O)–H to in situ formed p-QM-like ion pairs from 2-benzofuryl-ols to C3-phosphinoyl hydrobenzofurans

L. Chen, Y. Zou, S. Zheng, X. Liu, H. Yang, J. Zhang, Y. Zeng, L. Duan, Z. Wen and H. Ni, Org. Chem. Front., 2021, 8, 1756 DOI: 10.1039/D1QO00076D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements