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dc.contributor.authorNi, Shengyang
dc.contributor.authorMuñoz Padial, Natalia 
dc.date.accessioned2020-02-27T09:24:58Z
dc.date.available2020-02-27T09:24:58Z
dc.date.issued2019
dc.identifier.citationS. Ni, N. M. Padial, C. Kingston, J. C. Vantourout, D. C. Schmitt, J.T. Edwards, M. M. Kruszyk, R. R. Merchant, P. K. Mykhailiuk, B. B. Sanchez, S. Yang, M. A. Perry, G. M. Gallego, J. J. Mousseau, M. R. Collins, R. J. Cherney, P. S. Lebed, J. S. Chen, T. Qin, P. S. Baran. “A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines”. J. Am. Chem. Soc. 2019, 141, 6726–6739. [https://pubs.acs.org/doi/10.1021/jacs.9b02238]es_ES
dc.identifier.urihttp://hdl.handle.net/10481/59869
dc.descriptionWe would like to thank Enamine Ltd for providing samples of several acids. We are grateful to Dr. Dee- Hua Huang and Dr. Laura Pasternack (Scripps Research) for assistance with nuclear magnetic resonance (NMR) spectroscopy and Mr. Andrew Badwal (Pfizer) for high throughput purification. We also thank Stephen Harwood (Scripps Research) for helpful advice and David Hill and Prof. Donna Blackmond (both Scripps Research) for assistance with the mechanistic studies.es_ES
dc.description.abstractHistorically accessed through two-electron, anionic chemistry, ketones, alcohols, and amines are of foundational importance to the practice of organic synthesis. After placing this work in proper historical context, this Article reports the development, full scope, and a mechanistic picture for a strikingly different way of forging such functional groups. Thus, carboxylic acids, once converted to redox-active esters (RAEs) can be utilized as formally nucleophilic coupling partners with other carboxylic derivatives (to produce ketones), imines (to produce benzylic amines), or aldehydes (to produce alcohols). The reactions are uniformly mild, operationally simple, and, in the case of ketone synthesis, broad in scope (including several applications to the simplification of synthetic problems and to parallel synthesis). Finally, an extensive mechanistic study of the ketone synthesis is performed to trace the elementary steps of the catalytic cycle and provide the end-user with a clear and understandable rationale for the selectivity, role of additives, and underlying driving forces involved.es_ES
dc.description.sponsorshipFinancial support for this work was provided by NIH (GM- 118176), the China Scholarship Council (CSC, S.N.), the Marie Skłodowska-Curie Global Fellowships (749359-EnanSET, N.M.P) within the European Union research and innovation framework programme (2014-2020), and the fulbright Scholar Program (P.K.M.).es_ES
dc.language.isoenges_ES
dc.publisherAmerican Chemical Societyes_ES
dc.rightsAtribución-NoComercial-SinDerivadas 3.0 España*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.titleA Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amineses_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses_ES
dc.identifier.doi10.1021/jacs.9b02238


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