Ligand-free reductive coupling of aldehydes with 1,3-dienes using a sulfur-modified Au-supported nickel nanoparticle catalyst

Ohta, Ryosuke; Shio, Yasunori; Akiyama, Toshiki; Yamada, Makito; Harada, Kaoru; Arisawa, Mitsuhiro

doi:10.1039/d3nj00354j

“…In contrast, phosphate with a trimethylsilyl group tends to undergo isomerization at the double bond, resulting in Z -diene 4 – 2g . The simplicity and effectiveness of this methodology are further underscored by its widespread adoption in numerous publications [ 47 , 48 , 49 , 50 , 51 , 52 , 53 ].…”

Section: Organophosphates As Electrophiles In Transition-metal-cataly...mentioning

confidence: 99%

Organophosphates as Versatile Substrates in Organic Synthesis

Oeser,

Tobrman

2024

Molecules

0

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This review summarizes the applications of organophosphates in organic synthesis. After a brief introduction, it discusses cross-coupling reactions, including both transition-metal-catalyzed and transition-metal-free substitution reactions. Subsequently, oxidation and reduction reactions are described. In addition, this review highlights the applications of organophosphates in the synthesis of natural compounds, demonstrating their versatility and importance in modern synthetic chemistry.

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Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

Zeng,

Lin,

Shu

2024

Angewandte Chemie

0

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Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.

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Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

Zeng,

Lin,

Shu

2024

Angew Chem Int Ed

2

0

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Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.

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Ligand-free reductive coupling of aldehydes with 1,3-dienes using a sulfur-modified Au-supported nickel nanoparticle catalyst

Abstract: Ligand-free reductive coupling of aldehydes with 1,3-diene was successfully developed using the nickel nanoparticle catalyst SANi, Sulfur-modified Au-supported Nickel. Leakage of nickel species into the reaction solution is minimal. SANi...

Cited by 3 publications

References 51 publications

Organophosphates as Versatile Substrates in Organic Synthesis

Organophosphates as Versatile Substrates in Organic Synthesis

Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

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