Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents

Yashwant Bhaskar Pandit; Yan Ting Jiang; Jia Jyun Jian; Tai Chi Chen; Tung Chun Kuo; Mu Jeng Cheng; Rai Shung Liu

doi:10.1039/d1qo00026h

Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents

Yashwant Bhaskar Pandit, Yan Ting Jiang, Jia Jyun Jian, Tai Chi Chen, Tung Chun Kuo, Mu Jeng Cheng, Rai Shung Liu

Department of Chemistry

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

3 Citations (Scopus)

Abstract

This work reports the gold-catalyzed [5 + 2]-annulations of commonly used anthranils with 1,3-diynamides, yielding quiniline oxides as the main products. Previously, these [5 + 2]-annulations were operable only for ynamides and special anthranils bearing C(6)-substituents. The preferable chemoselectivity is attributed to the electron-withdrawing effects of aryltosylamides and alkynes, increasing the electrophilicity of the less hindered α-imino gold carbenes.

Original language	English
Pages (from-to)	2563-2568
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	8
Issue number	11
DOIs	https://doi.org/10.1039/d1qo00026h
Publication status	Published - 2021 Jun 7

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1039/d1qo00026h

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title = "Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents",

abstract = "This work reports the gold-catalyzed [5 + 2]-annulations of commonly used anthranils with 1,3-diynamides, yielding quiniline oxides as the main products. Previously, these [5 + 2]-annulations were operable only for ynamides and special anthranils bearing C(6)-substituents. The preferable chemoselectivity is attributed to the electron-withdrawing effects of aryltosylamides and alkynes, increasing the electrophilicity of the less hindered α-imino gold carbenes.",

author = "Pandit, {Yashwant Bhaskar} and Jiang, {Yan Ting} and Jian, {Jia Jyun} and Chen, {Tai Chi} and Kuo, {Tung Chun} and Cheng, {Mu Jeng} and Liu, {Rai Shung}",

note = "Funding Information: We thank the Ministry of Education (MOE 106N506CE1) and the Ministry of Science and Technology (MOST 107-3017-F-007-002), Taiwan, for the financial support of this work. Publisher Copyright: {\textcopyright} 2021 the Partner Organisations.",

year = "2021",

month = jun,

day = "7",

doi = "10.1039/d1qo00026h",

language = "English",

volume = "8",

pages = "2563--2568",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

number = "11",

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TY - JOUR

T1 - Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents

AU - Pandit, Yashwant Bhaskar

AU - Jiang, Yan Ting

AU - Jian, Jia Jyun

AU - Chen, Tai Chi

AU - Kuo, Tung Chun

AU - Cheng, Mu Jeng

AU - Liu, Rai Shung

N1 - Funding Information: We thank the Ministry of Education (MOE 106N506CE1) and the Ministry of Science and Technology (MOST 107-3017-F-007-002), Taiwan, for the financial support of this work. Publisher Copyright: © 2021 the Partner Organisations.

PY - 2021/6/7

Y1 - 2021/6/7

N2 - This work reports the gold-catalyzed [5 + 2]-annulations of commonly used anthranils with 1,3-diynamides, yielding quiniline oxides as the main products. Previously, these [5 + 2]-annulations were operable only for ynamides and special anthranils bearing C(6)-substituents. The preferable chemoselectivity is attributed to the electron-withdrawing effects of aryltosylamides and alkynes, increasing the electrophilicity of the less hindered α-imino gold carbenes.

AB - This work reports the gold-catalyzed [5 + 2]-annulations of commonly used anthranils with 1,3-diynamides, yielding quiniline oxides as the main products. Previously, these [5 + 2]-annulations were operable only for ynamides and special anthranils bearing C(6)-substituents. The preferable chemoselectivity is attributed to the electron-withdrawing effects of aryltosylamides and alkynes, increasing the electrophilicity of the less hindered α-imino gold carbenes.

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U2 - 10.1039/d1qo00026h

DO - 10.1039/d1qo00026h

M3 - Article

AN - SCOPUS:85107413995

VL - 8

SP - 2563

EP - 2568

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 11

ER -

Gold-catalyzed [5 + 2]-annulations of 1,3-diyn-1-amides with anthranils bearing no C(6)-substituents

Abstract

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