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Palladium-Catalyzed Remote ortho-C-H Alkenylation of Alkyl Aryl Sulfones: Access to Densely Functionalized Indane Derivatives

Author
Legarda, Pablo D.; García-Rubia, Alfonso; Gómez-Arrayás, Ramón; Carretero, Juan C.
Entity
UAM. Departamento de Química Orgánica
Publisher
Wiley-VCH Verlag
Date
2016-03-31
Citation
10.1002/adsc.201501129
Advanced Synthesis and Catalysis 358.7 (2016): 1065-1072
 
 
 
ISSN
1615-4150 (print); 1615-4169 (online)
DOI
10.1002/adsc.201501129
Funded by
We thank the Spanish Government (MINECO, CTQ2012- 35790) for financial support. P.D. L. thanks the Spanish Government (MINECO) for an FPU predoctoral fellowship
Project
Gobierno de España. CTQ2012- 35790
Editor's Version
http://dx.doi.org/10.1002/adsc.201501129
Subjects
2-pyridyl sulfones; C-H alkenylation; Indanes; Michael-type addition; Palladium; Química
URI
http://hdl.handle.net/10486/670656
Note
This is the peer-reviewed version of the following article: Advanced Synthesis and Catalysis 358.7 (2016): 1065-1072, which has been published in final form at http://dx.doi.org/10.1002/adsc.201501129. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving
Rights
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Abstract

A practical method for the palladium-cat-alyzed ortho-olefination of benzyl and phenethyl 2-pyridyl sulfones with electron-deficient alkenes using N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is described. The che-lating auxiliary (2-pyridyl)sulfonyl unit was demon-strated to be the key to the success of this reaction, which occurs efficiently with excellent regioselectiv-ity and monosubstitution selectivity. A variety of steric and electronic changes to both coupling part-ners is tolerated, including substitution at the ben-zylic position of the sulfone compound. Further-more, no appreciable loss of enantiopurity is ob-served when using non-racemic substrates. This method provides access to indane derivatives hold-ing three contiguous stereogenic centers with high diastereocontrol. The indane framework was con-structed by intramolecular Michael addition of the a-sulfonyl carbanion to the electrophilic alkene
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Google™ Scholar:Legarda, Pablo D. - García-Rubia, Alfonso - Gómez-Arrayás, Ramón - Carretero, Juan C.

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  • Producción científica en acceso abierto de la UAM [14411]

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