Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes

Tzu Hsuan Kuan; Trimurtulu Kotipalli; Cheng Chun Chen; Duen Ren Hou

doi:10.1039/d1ob01941d

Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes

Tzu Hsuan Kuan, Trimurtulu Kotipalli, Cheng Chun Chen, Duen Ren Hou

Department of Chemistry

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

3 Scopus citations

Abstract

Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.

Original language	English
Pages (from-to)	10390-10402
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	47
DOIs	https://doi.org/10.1039/d1ob01941d
State	Published - 21 Dec 2021

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10.1039/d1ob01941d

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )
Hou, D.-R. (PI)
1/08/19 → 31/07/20
Project: Research
Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)
Hou, D.-R. (PI)
1/08/18 → 31/07/19
Project: Research

CCDC 2068139: Experimental Crystal Structure Determination
Kuan, T.-H. (Contributor), Kotipalli, T. (Contributor), Chen, C.-C. (Contributor) & Hou, D.-R. (Contributor), Cambridge Crystallographic Data Centre, 2021
DOI: 10.5517/ccdc.csd.cc27f25y, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc27f25y&sid=DataCite
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title = "Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes",

abstract = "Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.",

author = "Kuan, {Tzu Hsuan} and Trimurtulu Kotipalli and Chen, {Cheng Chun} and Hou, {Duen Ren}",

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TY - JOUR

T1 - Addition of benzyl ethers to alkynes

T2 - A metal-free synthesis of 1: H -isochromenes

AU - Kuan, Tzu Hsuan

AU - Kotipalli, Trimurtulu

AU - Chen, Cheng Chun

AU - Hou, Duen Ren

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2021/12/21

Y1 - 2021/12/21

N2 - Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.

AB - Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (o-arylethynyl)benzyl ethers to form 1H-isochromenes at room temperature is reported. Further studies indicated that vinyl carbocations are the reaction intermediates which are stabilized by the conjugated aryl groups. Thus, O-addition of benzyl ethers/tetrahydropyrans to alkynes was achieved under metal-free, acidic conditions. These reaction conditions were compatible with an alkynyl Prins reaction; therefore, 1H-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.

UR - http://www.scopus.com/inward/record.url?scp=85121116545&partnerID=8YFLogxK

U2 - 10.1039/d1ob01941d

DO - 10.1039/d1ob01941d

M3 - 期刊論文

C2 - 34825694

AN - SCOPUS:85121116545

SN - 1477-0520

VL - 19

SP - 10390

EP - 10402

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 47

ER -

Addition of benzyl ethers to alkynes: A metal-free synthesis of 1: H -isochromenes

Abstract

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Projects

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )

Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)

Datasets

CCDC 2068139: Experimental Crystal Structure Determination

Cite this