Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides

[Image: see text] CuI and trans-N,N′-dimethylcyclohexyldiamine catalyze the single-step C–O bond cross-coupling between 1,2-di- and trisubstituted vinylic halides with functionalized alcohols, producing acyclic vinylic ethers. This stereospecific transformation selectively gives each of the (E)- and...

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Autores principales: Pham, San L., Kim, Taehee, McDonald, Frank E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367064/
https://www.ncbi.nlm.nih.gov/pubmed/37437300
http://dx.doi.org/10.1021/acs.orglett.3c01849
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author Pham, San L.
Kim, Taehee
McDonald, Frank E.
author_facet Pham, San L.
Kim, Taehee
McDonald, Frank E.
author_sort Pham, San L.
collection PubMed
description [Image: see text] CuI and trans-N,N′-dimethylcyclohexyldiamine catalyze the single-step C–O bond cross-coupling between 1,2-di- and trisubstituted vinylic halides with functionalized alcohols, producing acyclic vinylic ethers. This stereospecific transformation selectively gives each of the (E)- and (Z)-vinylic ether products from the corresponding vinyl halide precursors. This method is compatible with carbohydrate-derived primary and secondary alcohols and several other functional groups. The conditions are mild enough to reliably generate vinylic allylic ethers without promoting Claisen rearrangements.
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spelling pubmed-103670642023-07-26 Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides Pham, San L. Kim, Taehee McDonald, Frank E. Org Lett [Image: see text] CuI and trans-N,N′-dimethylcyclohexyldiamine catalyze the single-step C–O bond cross-coupling between 1,2-di- and trisubstituted vinylic halides with functionalized alcohols, producing acyclic vinylic ethers. This stereospecific transformation selectively gives each of the (E)- and (Z)-vinylic ether products from the corresponding vinyl halide precursors. This method is compatible with carbohydrate-derived primary and secondary alcohols and several other functional groups. The conditions are mild enough to reliably generate vinylic allylic ethers without promoting Claisen rearrangements. American Chemical Society 2023-07-12 /pmc/articles/PMC10367064/ /pubmed/37437300 http://dx.doi.org/10.1021/acs.orglett.3c01849 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Pham, San L.
Kim, Taehee
McDonald, Frank E.
Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title_full Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title_fullStr Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title_full_unstemmed Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title_short Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides
title_sort stereospecific cu(i)-catalyzed c–o cross-coupling synthesis of acyclic 1,2-di- and trisubstituted vinylic ethers from alcohols and vinylic halides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10367064/
https://www.ncbi.nlm.nih.gov/pubmed/37437300
http://dx.doi.org/10.1021/acs.orglett.3c01849
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AT mcdonaldfranke stereospecificcuicatalyzedcocrosscouplingsynthesisofacyclic12diandtrisubstitutedvinylicethersfromalcoholsandvinylichalides

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