Synthesis of Highly Functionalized Indoles and Indolones via Selectivity-Switchable Olefinations

Ting Hui Ding; Zu Feng Xiao; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.joc.7b03158

Synthesis of Highly Functionalized Indoles and Indolones via Selectivity-Switchable Olefinations

Ting Hui Ding, Zu Feng Xiao, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

University of Science and Technology of China

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

5 Scopus citations

Abstract

Highly functionalized indoles and indolones were prepared via selectivity-switchable mono- or diolefinations. The Julia olefination of the products followed by a Brønsted acid-prompted cyclization afforded indolones, whereas the indoles were obtained by a sequential Wittig olefination and electrocyclization. This method opens divergent access to highly functionalized nitrogen-containing bicyclic or tricyclic heterocycles.

Original language	English
Pages (from-to)	2467-2472
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	83
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.7b03158
State	Published - 16 Feb 2018

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title = "Synthesis of Highly Functionalized Indoles and Indolones via Selectivity-Switchable Olefinations",

abstract = "Highly functionalized indoles and indolones were prepared via selectivity-switchable mono- or diolefinations. The Julia olefination of the products followed by a Br{\o}nsted acid-prompted cyclization afforded indolones, whereas the indoles were obtained by a sequential Wittig olefination and electrocyclization. This method opens divergent access to highly functionalized nitrogen-containing bicyclic or tricyclic heterocycles.",

author = "Ding, {Ting Hui} and Xiao, {Zu Feng} and Qu, {Jian Ping} and Kang, {Yan Biao}",

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AU - Ding, Ting Hui

AU - Xiao, Zu Feng

AU - Qu, Jian Ping

AU - Kang, Yan Biao

PY - 2018/2/16

Y1 - 2018/2/16

N2 - Highly functionalized indoles and indolones were prepared via selectivity-switchable mono- or diolefinations. The Julia olefination of the products followed by a Brønsted acid-prompted cyclization afforded indolones, whereas the indoles were obtained by a sequential Wittig olefination and electrocyclization. This method opens divergent access to highly functionalized nitrogen-containing bicyclic or tricyclic heterocycles.

AB - Highly functionalized indoles and indolones were prepared via selectivity-switchable mono- or diolefinations. The Julia olefination of the products followed by a Brønsted acid-prompted cyclization afforded indolones, whereas the indoles were obtained by a sequential Wittig olefination and electrocyclization. This method opens divergent access to highly functionalized nitrogen-containing bicyclic or tricyclic heterocycles.

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U2 - 10.1021/acs.joc.7b03158

DO - 10.1021/acs.joc.7b03158

M3 - 文章

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SN - 0022-3263

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Synthesis of Highly Functionalized Indoles and Indolones via Selectivity-Switchable Olefinations

Abstract

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