Highly Regio- and Stereoselective Palladium(0)-Catalyzed Addition of Organoboronic Acids with 1,2-Allenic Sulfones, Sulfoxides, or Alkyl- or Aryl-Substituted Allenes in the Presence of Acetic Acid: An Efficient Synthesis of <i>E</i>-Alkenes

Guo, Hao; Ma, Shengming

doi:10.1055/s-2007-983822

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 Addition Of Boronic Acid1

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Cited by 2 publications

(1 citation statement)

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“…They also extended the method to 1,2-allenylphosphonates, 1,2-allenic sulfones and sulfoxides. 126 Scheme 53: Hydroarylation of allenes with aryl boronic acids and mechanistic studies.…”

Section:  Addition Of Boronic Acidmentioning

confidence: 99%

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

2020

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“…They also extended the method to 1,2-allenylphosphonates, 1,2-allenic sulfones and sulfoxides. 126 Scheme 53: Hydroarylation of allenes with aryl boronic acids and mechanistic studies.…”

Section:  Addition Of Boronic Acidmentioning

confidence: 99%

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

2020

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Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones

et al. 2021

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The regiospecific radical reactions of β-alkyl nitroalkenes with sulfonyl hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl nitroalkenes. The mechanism investigation revealed that the regioselectivity was controlled by the equilibrium of β-alkyl nitroalkenes and allyl nitro compounds.

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Highly Regio- and Stereoselective Palladium(0)-Catalyzed Addition of Organoboronic Acids with 1,2-Allenic Sulfones, Sulfoxides, or Alkyl- or Aryl-Substituted Allenes in the Presence of Acetic Acid: An Efficient Synthesis of E-Alkenes

Abstract: P a l l a d i u m (0)-C a t a l y z e d A d d i t i o n o f O r g a n o b o r o n i c A c i d s w i t h A l l e n e s

Cited by 2 publications

References 7 publications

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

Metal-Catalyzed Intermolecular Hydrofunctionalization of Allenes: Easy Access to Allylic Structures via the Selective Formation of C–N, C–C, and C–O Bonds

Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones

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