Synthesis of propargyl silanes from terminal alkynes<i>via</i>a migratory Sonogashira reaction

Puriņš, Mikus; Eichenberger, L.; Waser, Jérôme

doi:10.1039/d3cc01847d

Chem. Commun.

2023

DOI: 10.1039/d3cc01847d

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Synthesis of propargyl silanes from terminal alkynesviaa migratory Sonogashira reaction

Mikus Puriņš

L. Eichenberger

Jérôme Waser

Abstract: Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an...

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2024

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Cited by 2 publications

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Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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This contribution offers a comprehensive overview of methods for forging sp C–Si bonds. Over time, alkynylsilanes (silylacetylenes), once considered mere byproducts of hydrosilylation processes, have become essential building blocks in organic synthesis. This literature review traces the evolution of their synthesis, from traditional methodologies relying on organolithium and organomagnesium compounds to more advanced cross‐coupling reactions involving hydro‐ and carbosilanes. Focused primarily on the past 25 years (2000‐2024), it also extensively references significant historical breakthroughs. By analyzing synthetic methodologies, the review not only offers a comprehensive survey of the current state of knowledge but also identifies areas for improvement. Furthermore, to emphasize the importance of 1‐alkynylsilanes (1‐silyl‐1‐alkynes), selected applications of these compounds are highlighted, confirming their significant potential in organic synthesis.

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Synthesis of Alkynylsilanes: A Review of the State of the Art

Kuciński

2024

Adv Synth Catal

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Stereodivergent access to non-natural α-amino acids via enantio- and Z / E -selective catalysis

Li,

Zheng,

et al. 2024

Science

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The precise control of Z and E configurations of the carbon-carbon double bond in alkene synthesis has long been a fundamental challenge in synthetic chemistry, even more pronounced when simultaneously striving to achieve enantioselectivity [( Z , R ), ( Z , S ), ( E , R ), ( E , S )]. Moreover, enantiopure non-natural α-amino acids are highly sought after in organic and medicinal chemistry. In this study, we report a ligand-controlled stereodivergent synthesis of non-natural α-quaternary amino acids bearing trisubstituted alkene moieties in high yields with excellent enantioselectivity and Z / E selectivities. This success is achieved through a palladium/copper–cocatalyzed three-component assembly of readily available aryl iodides, allenes, and aldimine esters by simply tuning the chiral ligands of the palladium and copper catalysts.

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Synthesis of propargyl silanes from terminal alkynesviaa migratory Sonogashira reaction

Abstract: Herein we report a mild synthesis of propargyl silanes from terminal alkynes. We exploit a bromonaphthyl-substituted silane as a silylmethyl electrophile surrogate, which participates in a Sonogashira reaction after an...

Cited by 2 publications

References 31 publications

Synthesis of Alkynylsilanes: A Review of the State of the Art

Synthesis of Alkynylsilanes: A Review of the State of the Art

Stereodivergent access to non-natural α-amino acids via enantio- and Z / E -selective catalysis

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