One-Pot Synthesis of Terminal Alkynes from Alkenes

The direct synthesis of terminal alkynes from widely available terminal alkenes is an unmet challenge in organic synthesis. Here, we show that alkyl and aromatic terminal alkenes can be converted to the corresponding alkynes in a one-pot process consisting of a Ru-catalyzed dehydrogenative hydrosilylation, followed by an oxidative dehydrogenative reaction of the vinyl silane intermediate, enabled by the combination of PhIO with BF<sub>3</sub>. This formal alkene dehydrogenation reaction with commercially available reagents and under mild reaction conditions gives access to terminal alkynes in a simple manner, including acetylene.

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Publication Details

Journal
JACS Au
Published
2024-08-05
DOI
https://doi.org/10.1021/jacsau.4c00599
Citations
2
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.50

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article

One-Pot Synthesis of Terminal Alkynes from Alkenes

Antonio Leyva‐Pérez, Cristina Bilanin, Amravati S. Singh, Lluís Martínez-Belenguer
2 citations
JACS Au
Catalytic Alkyne Reactions
0.50
article

One-Pot Synthesis of Terminal Alkynes from Alkenes

Antonio Leyva‐Pérez, Cristina Bilanin, Amravati S. Singh, Lluís Martínez-Belenguer
article en
2 citations

Abstract

The direct synthesis of terminal alkynes from widely available terminal alkenes is an unmet challenge in organic synthesis. Here, we show that alkyl and aromatic terminal alkenes can be converted to the corresponding alkynes in a one-pot process consisting of a Ru-catalyzed dehydrogenative hydrosilylation, followed by an oxidative dehydrogenative reaction of the vinyl silane intermediate, enabled by the combination of PhIO with BF<sub>3</sub>. This formal alkene dehydrogenation reaction with commercially available reagents and under mild reaction conditions gives access to terminal alkynes in a simple manner, including acetylene.

JACS AuVol. 4(8)
Consejo Superior de Investigaciones Científicas (ES), Instituto de Tecnología Química (ES), Universitat Politècnica de València (ES)
Ministerio de Ciencia e Innovación, Universitat Politècnica de València
Openalex Percentile: Top 40%
Catalytic Alkyne Reactions
0.50
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One-Pot Synthesis of Terminal Alkynes from Alkenes — Antonio Leyva‐Pérez, Cristina Bilanin, et al. · JACS Au (2024) | TGRS Research Map | TGRS