Bismuth(III)-catalysed hydroalkylation of styrene with acetylacetone: a DFT-Based mechanistic study

Heavier main-group element-catalyzed reactions provide an increasingly attractive tool to perform transformations mimicking the behaviors of transition metal catalysts. Recently, Magre and Cornella reported a Bicatalyzed synthesis of aryl sulfonyl fluorides, which involves a fundamental organometallic step of SO 2 insertion into the BiÀ Ph bond. Our theoretical studies reveal that i) the ability of hypervalent coordination of the Bi(III) center allows facile coordination sphere expansion for the SO 2 coordination via one oxygen atom; and ii) the high polarity of the BiÀ Ph bond makes the Ph migration from the Bi(III) center feasible. These features enable the heavier main group element to resemble the transition metal having flexibility for ligand association and dissociation. Furthermore, iii) the available π electron pair of the migrating Ph group stabilizes the SO 2 insertion transition state by maintaining interaction with the Bi(III) center during migration. The insight helps us better understand the heavier main-group catalysis.

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Understanding the Organometallic Step: SO₂ Insertion into Bi(III)−C(Ph) Bond

Wong

Guo

Chan

et al. 2023

Chemistry An Asian Journal

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Tris(pentafluorophenyl)borane reusable catalyst for hydroalkylation of styrenes with 1, 3-dicarbonyl compounds in PEG

Garapati,

Redipalli,

Lakkoju

et al. 2025

Kuwait Journal of Science

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Bismuth(III)-catalysed hydroalkylation of styrene with acetylacetone: a DFT-Based mechanistic study

Cited by 2 publications

References 32 publications

Understanding the Organometallic Step: SO₂ Insertion into Bi(III)−C(Ph) Bond

Understanding the Organometallic Step: SO₂ Insertion into Bi(III)−C(Ph) Bond

Tris(pentafluorophenyl)borane reusable catalyst for hydroalkylation of styrenes with 1, 3-dicarbonyl compounds in PEG

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Bismuth(III)-catalysed hydroalkylation of styrene with acetylacetone: a DFT-Based mechanistic study

Cited by 2 publications

References 32 publications

Understanding the Organometallic Step: SO2 Insertion into Bi(III)−C(Ph) Bond

Understanding the Organometallic Step: SO2 Insertion into Bi(III)−C(Ph) Bond

Tris(pentafluorophenyl)borane reusable catalyst for hydroalkylation of styrenes with 1, 3-dicarbonyl compounds in PEG

Contact Info

Product

Resources

About

Understanding the Organometallic Step: SO₂ Insertion into Bi(III)−C(Ph) Bond

Understanding the Organometallic Step: SO₂ Insertion into Bi(III)−C(Ph) Bond