Regioselective Diboron-Mediated Semireduction of Terminal Allenes

Gates, Ashley Michelle; Santos, Webster L.

doi:10.1055/s-0039-1690207

Cited by 8 publications

(2 citation statements)

References 17 publications

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“…Other functional groups are reduced analogously by the Pd−H species [31] . Gates and Santos found that, in the presence of a palladium catalyst, THDB and water, allene semireduction proceeds in high yield to afford Z‐alkenes selectively [32] . Peng and Tang reported transfer hydrogenation from water to unsaturated carbonyls, quinones, and pyridinium salts forming the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines by THDB/water in the absence of metal catalyst [33] …”

Section: Reductant Properties and Transfer Hydrogenation Of Water/thdbmentioning

confidence: 99%

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

2023

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Diboron compounds with a BÀ B bond, discovered with B 2 Cl 4 a century ago, have been developed only since the turn of this century for catalyzed borylation reactions, mostly with the wellknow reagent bis(binacolato)diboron, (B 2 pin 2 ). On the other hand, chemistry of tetrahydroxydiboron (THDB), also named bis-boric acid, is relatively underdeveloped. In this review, the properties of THDB as a borylation, reductant (including transfer hydrogenation), catalyst, source of radicals and generator of H 2 from water upon hydrolysis are summarized.

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Section: Reductant Properties and Transfer Hydrogenation Of Water/thdbmentioning

confidence: 99%

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

2023

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“…In 2019, the Santos group reported Pd/C catalyzed regioselective semireduction of the terminal allene of 1,1-disubstituted allenes in the presence of B 2 (OH) 4 and H 2 O (eq 31). …”

Section: Application Of H2 Evolution Upon Diborane Hydrolysismentioning

confidence: 99%

A Deeper Understanding of H₂ Evolution Entirely from Water via Diborane Hydrolysis

Liu

Zhang

et al. 2023

ACS Materials Lett.

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Hydrogen (H2) has drawn extensive attention due to its superior gravimetric capacity density and eco-friendly nature. Nowadays, hydrogen is mainly produced by the steam reforming of natural gas, a process that leads to massive emissions of greenhouse gases. Very recently, H2 evolution upon hydrolysis of diboranes (e.g., B2(OH)4 and B2pin2) is promising because both H atoms of the released H2 are obtained from water. This is different from the hydrolysis of sodium borohydride, dimethylaminoborane, ammonia borane, and tetramethyldisiloxane, where an H2 is generated with only one H atom from H2O and the other one from hydrogen storage materials. Importantly, diborane hydrolysis in D2O could provide an easy and simple method for D2 evolution. In this minireview, an overview of H2 evolution upon diborane hydrolysis with an extraordinary emphasis on the recent developments in mechanism study and applications is presented. The future research emphasis and perspectives of H2 evolution upon diborane hydrolysis have been suggested for commercialization as well.

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Ligand‐Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Shayegan

Cui

2021

Chemistry A European J

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Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo-and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3semireduction, producing (E)-enamide derivatives.

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Regioselective Diboron-Mediated Semireduction of Terminal Allenes

Abstract: A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

Cited by 8 publications

References 17 publications

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

A Deeper Understanding of H₂ Evolution Entirely from Water via Diborane Hydrolysis

Ligand‐Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

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Regioselective Diboron-Mediated Semireduction of Terminal Allenes

Abstract: A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

Cited by 8 publications

References 17 publications

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H2 Generation

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H2 Generation

A Deeper Understanding of H2 Evolution Entirely from Water via Diborane Hydrolysis

Ligand‐Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

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Product

Resources

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Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

Tetrahydroxydiboron (Bis‐boric Acid): a Versatile Reagent for Borylation, Hydrogenation, Catalysis, Radical Reactions and H₂ Generation

A Deeper Understanding of H₂ Evolution Entirely from Water via Diborane Hydrolysis