Addition of benzyl ethers to alkynes: a metal-free synthesis of 1-isochromenes
Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of ( o -arylethynyl)benzyl ethers to form 1 H -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 -...
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| Published in | Organic & biomolecular chemistry Vol. 19; no. 47; pp. 139 - 142 |
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| Main Authors | , , , |
| Format | Journal Article |
| Published |
08.12.2021
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| Online Access | Get full text |
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| Abstract | Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (
o
-arylethynyl)benzyl ethers to form 1
H
-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, 1
H
-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.
The synthesis of 1
H
-isochromenes was achieved by addition of benzyl ethers to alkynes, activated with bromotrimethylsilane (TMSBr). |
|---|---|
| AbstractList | Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (
o
-arylethynyl)benzyl ethers to form 1
H
-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, 1
H
-isochromenes were produced directly from alkynyl benzaldehydes and alkynyl alcohols using a one-pot procedure.
The synthesis of 1
H
-isochromenes was achieved by addition of benzyl ethers to alkynes, activated with bromotrimethylsilane (TMSBr). |
| Author | Hou, Duen-Ren Chen, Cheng-Chun Kuan, Tzu-Hsuan Kotipalli, Trimurtulu |
| AuthorAffiliation | Department of Chemistry National Central University |
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| DOI | 10.1039/d1ob01941d |
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| Notes | 10.1039/d1ob01941d 1 For ESI and crystallographic data in CIF or other electronic format see DOI 13 C H} NMR spectra of all the new compounds. CCDC 2068139 6ad H and and the Electronic supplementary information (ESI) available: Experimental procedures, X-ray crystallography of |
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| PublicationTitle | Organic & biomolecular chemistry |
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| References_xml | – issn: 2014 end-page: 392-411 publication-title: Comprehensive Organic Synthesis II doi: Ogawa – issn: 2010 end-page: 123-155 publication-title: C-X Bond Formation doi: Hintermann – issn: 2014 end-page: 342-391 publication-title: Comprehensive Organic Synthesis II doi: Li Zhang – issn: 2011 issue: 43 publication-title: Hydrofunctionalization. Topics in Organometallic Chemistry doi: Huguet Echavarren |
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| Snippet | Bromotrimethylsilane (TMSBr)-promoted intramolecular cyclization of (
o
-arylethynyl)benzyl ethers to form 1
H
-isochromenes at room temperature is reported.... |
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| Title | Addition of benzyl ethers to alkynes: a metal-free synthesis of 1-isochromenes |
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