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Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones

(2014) ACS CATALYSIS. 4(8). p.2701-2705
Author
Organization
Abstract
We report a new catalytic protocol for the synthesis of gamma,delta-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.
Keywords
gold, hydroalkoxylation, Claisen rearrangement, homoallylic ketones, solvent-free, GAMMA, DELTA-UNSATURATED KETONES, ORGANIC TRANSFORMATIONS, CLAISEN REARRANGEMENT, ROOM-TEMPERATURE, GREEN CHEMISTRY, SILVER-FREE, COMPLEXES, ALKYNES, HYDROALKOXYLATION, CYCLIZATION

Citation

Please use this url to cite or link to this publication:

MLA
Gomez-Suarez, Adrian, et al. “Highly Efficient and Eco-Friendly Gold-Catalyzed Synthesis of Homoallylic Ketones.” ACS CATALYSIS, vol. 4, no. 8, 2014, pp. 2701–05.
APA
Gomez-Suarez, A., Gasperini, D., Vummaleti, S. V., Poater, A., Cavallo, L., & Nolan, S. (2014). Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones. ACS CATALYSIS, 4(8), 2701–2705.
Chicago author-date
Gomez-Suarez, Adrian, Danila Gasperini, Sai VC Vummaleti, Albert Poater, Luigi Cavallo, and Steven Nolan. 2014. “Highly Efficient and Eco-Friendly Gold-Catalyzed Synthesis of Homoallylic Ketones.” ACS CATALYSIS 4 (8): 2701–5.
Chicago author-date (all authors)
Gomez-Suarez, Adrian, Danila Gasperini, Sai VC Vummaleti, Albert Poater, Luigi Cavallo, and Steven Nolan. 2014. “Highly Efficient and Eco-Friendly Gold-Catalyzed Synthesis of Homoallylic Ketones.” ACS CATALYSIS 4 (8): 2701–2705.
Vancouver
1.
Gomez-Suarez A, Gasperini D, Vummaleti SV, Poater A, Cavallo L, Nolan S. Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones. ACS CATALYSIS. 2014;4(8):2701–5.
IEEE
[1]
A. Gomez-Suarez, D. Gasperini, S. V. Vummaleti, A. Poater, L. Cavallo, and S. Nolan, “Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones,” ACS CATALYSIS, vol. 4, no. 8, pp. 2701–2705, 2014.
@article{8168471,
  abstract     = {We report a new catalytic protocol for the synthesis of gamma,delta-unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.},
  author       = {Gomez-Suarez, Adrian and Gasperini, Danila and Vummaleti, Sai VC and Poater, Albert and Cavallo, Luigi and Nolan, Steven},
  issn         = {2155-5435},
  journal      = {ACS CATALYSIS},
  keywords     = {gold,hydroalkoxylation,Claisen rearrangement,homoallylic ketones,solvent-free,GAMMA,DELTA-UNSATURATED KETONES,ORGANIC TRANSFORMATIONS,CLAISEN REARRANGEMENT,ROOM-TEMPERATURE,GREEN CHEMISTRY,SILVER-FREE,COMPLEXES,ALKYNES,HYDROALKOXYLATION,CYCLIZATION},
  language     = {eng},
  number       = {8},
  pages        = {2701--2705},
  title        = {Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones},
  url          = {http://dx.doi.org/10.1021/cs500806m},
  volume       = {4},
  year         = {2014},
}

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