Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.

doi:10.1021/JA056112D

Paper

Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.

Published Jan 17, 2006 · Hong-Bo Qin, Noriyuki Yamagiwa, S. Matsunaga

Journal of the American Chemical Society

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109

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Abstract

A Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system efficiently promoted intermolecular 1:1 hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides to afford allylic amines in good yield (up to 96%). Reaction proceeded with 0.5-10 mol % catalyst loading at 25-100 degrees C (generally at 50 degrees C) in 1,4-dioxane within 24 h. The Bi(OTf)(3)/Cu(CH(3)CN)(4)PF(6) system constitutes a new entry into series of intermolecular hydroamination catalysis. Mechanistic studies and the postulated reaction mechanism are also discussed.

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Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with various carbamates, sulfonamides, and carboxamides efficiently produces allylic amines in good yield (up to 96%) within 24 hours at 25-100 degrees C in 1,4

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Bismuth-catalyzed intermolecular hydroamination of 1,3-dienes with carbamates, sulfonamides, and carboxamides.

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References

Citations

Synthesis of bismuthanyl-substituted monomeric triel hydrides

Bismuthanylborane monomers and bismuthanylgallane were synthesized using salt metathesis reactions, displaying high sensitivity to air and light, and slowly decompose in solution at 80°C.

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Reactions of carboxamides with vinylsilanes under oxidative conditions

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Bismuth subnitrate is a simple and efficient catalyst for the atom-economical synthesis of methyl ketones via Markovnikov-type alkyne hydration, offering practicality and sustainability without the need for special additives or harmful reagents.

Silver Salt-Mediated Allylation Reactions Using Allyl Bromides.

Silver salt-mediated allylation reactions using allyl bromides provide a facile, efficient, and chemoselective method for synthesis of various allylic amides under mild conditions.

CuIBiOI is an efficient novel catalyst in Ullmann-type CN couplings with wide scope—A rare non-photocatalyic application

CuIBiOI is an efficient, non-photocatalytic catalyst for Ullmann-type CN couplings, offering a green, recyclable method for a wide range of aryl halides.

Molecular Bismuth Cations: Assessment of Soft Lewis Acidity

Cationic bismuth compounds are potent soft Lewis acids that prefer Lewis pair formation with a soft (S/Se-based) donor rather than a hard (O/N-based) donor.