β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles

Kidonakis, Marios; Neochoritis, Constantinos G.; Stratakis, Manolis

doi:10.1039/d0ob01806f

Cited by 4 publications

(2 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[112] Recently, they reported a β-borylation method for α,β-unsaturated esters, andamides catalyzed by TiO 2 supported Au nanoparticles (Scheme 23). [113] Unlike all known metal-catalyzed analogous reactions, here the boryl moiety acts as a nucleophile under Au NP-catalyzed conditions, resulting in the conjugate β-borylation. After coordination to the substrate, selective delivery of boron and silicon moieties to the C and O atom respectively, gives the silaboration product.…”

Section: Gold Nanoparticle Catalyzed β-Borylationmentioning

confidence: 99%

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Das

Mahato

Hazra

et al. 2022

The Chemical Record

View full text Add to dashboard Cite

Organoboron compounds are highly important and versatile synthetic intermediates for the preparation of a wide range of organic molecules. Organoboron compounds have drawn significant attention among organic chemists due to their Lewis acidic property, non-toxicity, and commercial availability. Over the last several decades, there has been a substantial development of new organoboron compounds, useful in organic synthesis. Among all other organoboron compounds, β-boryl carbonyl compounds are the important ones. The β-boryl compounds have appeared as promising intermediates for various synthetic transformations. The 1,4-conjugate addition of diboron reagents to carbon-carbon double bond in the presence of different transition-metal catalysts has been extensively reported by various research groups across the globe. This mini-review outlines the numerous racemic as well as asymmetric β-borylation methods developed to date.

show abstract

Section: Gold Nanoparticle Catalyzed β-Borylationmentioning

confidence: 99%

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Das

Mahato

Hazra

et al. 2022

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…Therefore, they are regarded as crucial reaction precursors to prepare organoboron compounds via hydroboration reactions in organic synthesis . Various transition metals, such as nickel, platinum, gold, rhodium, and copper, ,, have been used as catalysts to facilitate these hydroboration reactions. However, these transition metals exhibit certain limitations.…”

Section: Introductionmentioning

confidence: 99%

Cu(II)-Catalyzed Hydroboration Reactions of 1,1-Disubstituted α,β-Unsaturated Ketones, Esters, and Amides in Pure Water

Zhao,

Li,

Zhou

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

Electrochemical Borylation of Electron‐Deficient Alkenes and Allenoates

2023

View full text Add to dashboard Cite

The electrochemical borylation of electro‐deficient alkenes and allenoates is disclosed. In an undivided cell and under galvanostatic conditions a panel of Michael acceptor and allenoates was readily reacted. The reaction offered an access to versatile borylated building blocks in good to excellent yields (20 examples, 47 % to 91 % yields). A plausible reaction mechanism, based on the literature precedent was suggested.

show abstract

β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles

Abstract: Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via intermediate formation of the labile silaboration adducts....

Cited by 4 publications

References 58 publications

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles

Cu(II)-Catalyzed Hydroboration Reactions of 1,1-Disubstituted α,β-Unsaturated Ketones, Esters, and Amides in Pure Water

Electrochemical Borylation of Electron‐Deficient Alkenes and Allenoates

Contact Info

Product

Resources

About