Facile synthesis of 3-aryloxindoles via Brønsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles

Changwei Zhai; Dong Xing; Changcheng Jing; Jun Zhou; Chengjin Wang; Dongwei Wang; Wenhao Hu

doi:10.1021/ol5010752

Facile synthesis of 3-aryloxindoles via Brønsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles

Changwei Zhai, Dong Xing, Changcheng Jing, Jun Zhou, Chengjin Wang, Dongwei Wang, Wenhao Hu

School of Chemistry and Molecular Engineering

East China Normal University

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

83 Scopus citations

Abstract

A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.

Original language	English
Pages (from-to)	2934-2937
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	11
DOIs	https://doi.org/10.1021/ol5010752
State	Published - 6 Jun 2014

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title = "Facile synthesis of 3-aryloxindoles via Br{\o}nsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles",

abstract = "A simple metal-free method for the synthesis of 3-aryloxindoles via Br{\o}nsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.",

author = "Changwei Zhai and Dong Xing and Changcheng Jing and Jun Zhou and Chengjin Wang and Dongwei Wang and Wenhao Hu",

year = "2014",

month = jun,

day = "6",

doi = "10.1021/ol5010752",

language = "英语",

volume = "16",

pages = "2934--2937",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Facile synthesis of 3-aryloxindoles via Brønsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles

AU - Zhai, Changwei

AU - Xing, Dong

AU - Jing, Changcheng

AU - Zhou, Jun

AU - Wang, Chengjin

AU - Wang, Dongwei

AU - Hu, Wenhao

PY - 2014/6/6

Y1 - 2014/6/6

N2 - A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.

AB - A simple metal-free method for the synthesis of 3-aryloxindoles via Brønsted acid catalyzed aromatic C-H functionalization of electron-rich arenes with 3-diazooxindoles is developed. In the presence of a catalytic amount of TfOH, a series of 3-aryloxindoles are synthesized as single regioisomers in good to excellent yields. This transformation is proposed to proceed through acid-catalyzed protonation of 3-diazooxindoles into diazonium ions followed by Friedel-Crafts-type alkylation of arenes.

UR - https://www.scopus.com/pages/publications/84902081258

U2 - 10.1021/ol5010752

DO - 10.1021/ol5010752

M3 - 文章

C2 - 24831829

AN - SCOPUS:84902081258

SN - 1523-7060

VL - 16

SP - 2934

EP - 2937

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Facile synthesis of 3-aryloxindoles via Brønsted acid catalyzed friedel-crafts alkylation of electron-rich arenes with 3-diazooxindoles

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