Highly efficient and eco-friendly gold-catalyzed synthesis of homoallylic ketones
- Author
- Adrian Gomez-Suarez, Danila Gasperini, Sai VC Vummaleti, Albert Poater, Luigi Cavallo and Steven Nolan (UGent)
- 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: http://hdl.handle.net/1854/LU-8168471
- 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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