Metal-free tandem Friedel-Crafts/lactonization reaction to benzofuranones bearing a quaternary center at C3 position

Long Chen; Feng Zhou; Tao Da Shi; Jian Zhou

doi:10.1021/jo300395x

Metal-free tandem Friedel-Crafts/lactonization reaction to benzofuranones bearing a quaternary center at C3 position

Long Chen
, Feng Zhou
, Tao Da Shi
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

59 Scopus citations

Abstract

A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO ₄ was reported. A variety of tertiary α-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. ¹H NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.

Original language	English
Pages (from-to)	4354-4362
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	77
Issue number	9
DOIs	https://doi.org/10.1021/jo300395x
State	Published - 4 May 2012

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title = "Metal-free tandem Friedel-Crafts/lactonization reaction to benzofuranones bearing a quaternary center at C3 position",

abstract = "A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO 4 was reported. A variety of tertiary α-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. 1H NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.",

author = "Long Chen and Feng Zhou and Shi, \{Tao Da\} and Jian Zhou",

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AU - Chen, Long

AU - Zhou, Feng

AU - Shi, Tao Da

AU - Zhou, Jian

PY - 2012/5/4

Y1 - 2012/5/4

N2 - A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO 4 was reported. A variety of tertiary α-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. 1H NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.

AB - A metal-free tandem Friedel-Crafts/lactonization reaction to 3,3-diaryl or 3-alkyl-3-aryl benzofuranones catalyzed by HClO 4 was reported. A variety of tertiary α-hydroxy acid esters could readily react with substituted phenols to afford the desired products in rich diversity. The synthetic utility of the products was demonstrated by the synthesis of polycyclic compounds. 1H NMR studies supported that this tandem reaction proceeded via tandem Friedel-Crafts/lactonization sequence.

UR - https://www.scopus.com/pages/publications/84860603664

U2 - 10.1021/jo300395x

DO - 10.1021/jo300395x

M3 - 文章

AN - SCOPUS:84860603664

SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

Metal-free tandem Friedel-Crafts/lactonization reaction to benzofuranones bearing a quaternary center at C3 position

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