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 ene. 2021
Accepted
11 feb. 2021
First published
18 feb. 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

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