Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

Cheng Chun Chen; Tzu Hsuan Kuan; Wen Wei Yuan; Shih En Chen; Jui Chen Fu; Yang Xun Chen; Hui Hsu Gavin Tsai; Duen Ren Hou

doi:10.1002/adsc.202200977

Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

Cheng Chun Chen, Tzu Hsuan Kuan, Wen Wei Yuan, Shih En Chen, Jui Chen Fu, Yang Xun Chen, Hui Hsu Gavin Tsai, Duen Ren Hou

Department of Chemistry

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

2 Scopus citations

Abstract

Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by ¹H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate. (Figure presented.).

Original language	English
Pages (from-to)	4122-4134
Number of pages	13
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	23
DOIs	https://doi.org/10.1002/adsc.202200977
State	Published - 8 Dec 2022

Keywords

benzannulation
isochromenylium
naphthalene
propargyl alcohol

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10.1002/adsc.202200977

CCDC 2176243: Experimental Crystal Structure Determination
Chen, C.-C. (Contributor), Kuan, T.-H. (Contributor), Yuan, W.-W. (Contributor), Chen, S.-E. (Contributor), Fu, J.-C. (Contributor), Chen, Y.-X. (Contributor), Gavin Tsai, H.-H. (Contributor) & Hou, D.-R. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2c1kdd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2c1kdd&sid=DataCite
Dataset
CCDC 2123951: Experimental Crystal Structure Determination
Chen, C.-C. (Contributor), Kuan, T.-H. (Contributor), Yuan, W.-W. (Contributor), Chen, S.-E. (Contributor), Fu, J.-C. (Contributor), Chen, Y.-X. (Contributor), Gavin Tsai, H.-H. (Contributor) & Hou, D.-R. (Contributor), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc2994kb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2994kb&sid=DataCite
Dataset

Cite this

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title = "Br{\o}nsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol",

abstract = "Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate. (Figure presented.).",

keywords = "benzannulation, isochromenylium, naphthalene, propargyl alcohol",

author = "Chen, {Cheng Chun} and Kuan, {Tzu Hsuan} and Yuan, {Wen Wei} and Chen, {Shih En} and Fu, {Jui Chen} and Chen, {Yang Xun} and {Gavin Tsai}, {Hui Hsu} and Hou, {Duen Ren}",

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doi = "10.1002/adsc.202200977",

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T1 - Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

AU - Chen, Cheng Chun

AU - Kuan, Tzu Hsuan

AU - Yuan, Wen Wei

AU - Chen, Shih En

AU - Fu, Jui Chen

AU - Chen, Yang Xun

AU - Gavin Tsai, Hui Hsu

AU - Hou, Duen Ren

PY - 2022/12/8

Y1 - 2022/12/8

N2 - Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate. (Figure presented.).

AB - Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1-naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate. (Figure presented.).

KW - benzannulation

KW - isochromenylium

KW - naphthalene

KW - propargyl alcohol

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U2 - 10.1002/adsc.202200977

DO - 10.1002/adsc.202200977

M3 - 期刊論文

AN - SCOPUS:85143231604

SN - 1615-4150

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JO - Advanced Synthesis and Catalysis

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IS - 23

ER -

Brønsted Acid-Promoted Benzannulation of o-Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

Abstract

Keywords

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Datasets

CCDC 2176243: Experimental Crystal Structure Determination

CCDC 2123951: Experimental Crystal Structure Determination

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