Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes

Regioselective anti-allylindation of alkynes was achieved using InBr(3) and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes...

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Autores principales: Nishimoto, Yoshihiro, Yi, Junyi, Takata, Tatsuaki, Baba, Akio, Yasuda, Makoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222668/
https://www.ncbi.nlm.nih.gov/pubmed/30060532
http://dx.doi.org/10.3390/molecules23081884
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author Nishimoto, Yoshihiro
Yi, Junyi
Takata, Tatsuaki
Baba, Akio
Yasuda, Makoto
author_facet Nishimoto, Yoshihiro
Yi, Junyi
Takata, Tatsuaki
Baba, Akio
Yasuda, Makoto
author_sort Nishimoto, Yoshihiro
collection PubMed
description Regioselective anti-allylindation of alkynes was achieved using InBr(3) and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I(2) to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene.
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spelling pubmed-62226682018-11-13 Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes Nishimoto, Yoshihiro Yi, Junyi Takata, Tatsuaki Baba, Akio Yasuda, Makoto Molecules Communication Regioselective anti-allylindation of alkynes was achieved using InBr(3) and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I(2) to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene. MDPI 2018-07-27 /pmc/articles/PMC6222668/ /pubmed/30060532 http://dx.doi.org/10.3390/molecules23081884 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Nishimoto, Yoshihiro
Yi, Junyi
Takata, Tatsuaki
Baba, Akio
Yasuda, Makoto
Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title_full Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title_fullStr Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title_full_unstemmed Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title_short Regio- and Stereoselective Allylindation of Alkynes Using InBr(3) and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes
title_sort regio- and stereoselective allylindation of alkynes using inbr(3) and allylic silanes: synthesis, characterization, and application of 1,4-dienylindiums toward skipped dienes
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222668/
https://www.ncbi.nlm.nih.gov/pubmed/30060532
http://dx.doi.org/10.3390/molecules23081884
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