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Nickel-catalyzed α-allylation of aldehydes and tandem aldol condensation/allylation reaction with allylic alcohols

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Abstract
An additive-free nickel-catalyzed alpha-allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol% of in situ formed nickel complex in methanol, and water is the sole by-product of the reaction. The experimental conditions allow the conversion of various alpha-branched aldehydes and alpha, beta-unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/alpha-allylation reaction.
Keywords
aldehydes, allylic alcohols, allylations, homogeneous catalysis, nickel, CONVERGENT TOTAL-SYNTHESIS, TRANSITION-METAL, SUBSTITUTION-REACTIONS, BRANCHED ALDEHYDES, SOFT NUCLEOPHILES, GREEN CHEMISTRY, ALKYLATION, PALLADIUM, ACID, AMINATION

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Chicago
Bernhard, Yann, Brodie Thomson, Vincent Ferey, and Mathieu Sauthier. 2017. “Nickel-catalyzed Α-allylation of Aldehydes and Tandem Aldol Condensation/allylation Reaction with Allylic Alcohols.” Angewandte Chemie-international Edition 56 (26): 7460–7464.
APA
Bernhard, Y., Thomson, B., Ferey, V., & Sauthier, M. (2017). Nickel-catalyzed α-allylation of aldehydes and tandem aldol condensation/allylation reaction with allylic alcohols. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56(26), 7460–7464.
Vancouver
1.
Bernhard Y, Thomson B, Ferey V, Sauthier M. Nickel-catalyzed α-allylation of aldehydes and tandem aldol condensation/allylation reaction with allylic alcohols. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2017;56(26):7460–4.
MLA
Bernhard, Yann et al. “Nickel-catalyzed Α-allylation of Aldehydes and Tandem Aldol Condensation/allylation Reaction with Allylic Alcohols.” ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.26 (2017): 7460–7464. Print.
@article{8612113,
  abstract     = {An additive-free nickel-catalyzed alpha-allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol\% of in situ formed nickel complex in methanol, and water is the sole by-product of the reaction. The experimental conditions allow the conversion of various alpha-branched aldehydes and alpha, beta-unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/alpha-allylation reaction.},
  author       = {Bernhard, Yann and Thomson, Brodie and Ferey, Vincent and Sauthier, Mathieu},
  issn         = {1433-7851},
  journal      = {ANGEWANDTE CHEMIE-INTERNATIONAL EDITION},
  language     = {eng},
  number       = {26},
  pages        = {7460--7464},
  title        = {Nickel-catalyzed \ensuremath{\alpha}-allylation of aldehydes and tandem aldol condensation/allylation reaction with allylic alcohols},
  url          = {http://dx.doi.org/10.1002/anie.201703486},
  volume       = {56},
  year         = {2017},
}

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