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

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

5 引文斯高帕斯（Scopus）

摘要

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.

原文	???core.languages.en_GB???
頁（從 - 到）	10390-10402
頁數	13
期刊	Organic and Biomolecular Chemistry
卷	19
發行號	47
DOIs	https://doi.org/10.1039/d1ob01941d
出版狀態	已出版 - 21 12月 2021

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10.1039/d1ob01941d

天然物合成與氮環丙烷相關合成方法之發展(2/2)
Hou, D.-R. (PI)
1/08/19 → 31/07/20
研究計畫: Research
天然物合成與氮丙烷相關合成方法之發展
Hou, D.-R. (PI)
1/08/18 → 31/07/19
研究計畫: Research

CCDC 2068139: Experimental Crystal Structure Determination
Kuan, T.-H. (貢獻者), Kotipalli, T. (貢獻者), Chen, C.-C. (貢獻者) & Hou, D.-R. (貢獻者), 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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引用此

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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\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2021",

month = dec,

day = "21",

doi = "10.1039/d1ob01941d",

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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 - https://www.scopus.com/pages/publications/85121116545

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

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天然物合成與氮環丙烷相關合成方法之發展(2/2)

天然物合成與氮丙烷相關合成方法之發展

資料集

CCDC 2068139: Experimental Crystal Structure Determination

引用此