{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T19:10:30Z","timestamp":1790709030589,"version":"4.1.0"},"reference-count":76,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2020,4,26]],"date-time":"2020-04-26T00:00:00Z","timestamp":1587859200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn\/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic \u03b1,\u03b2-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive \u03b2-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, \u03b1,\u03b2-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn\/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7\u00b0 recycling rounds).<\/jats:p>","DOI":"10.3390\/molecules25092018","type":"journal-article","created":{"date-parts":[[2020,4,29]],"date-time":"2020-04-29T01:24:18Z","timestamp":1588123458000},"page":"2018","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors"],"prefix":"10.3390","volume":"25","author":[{"given":"Francesca Giulia","family":"Nacca","sequence":"first","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences University of Perugia Via del Liceo 1, 06123 Perugia, Italy"},{"name":"Centre for Synthesis and Chemical Biology, School of Chemistry University College Dublin, Dublin D04, N2E5, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8490-7720","authenticated-orcid":false,"given":"Bonifacio","family":"Monti","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences University of Perugia Via del Liceo 1, 06123 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7920-3289","authenticated-orcid":false,"given":"Eder Jo\u00e3o","family":"Lenard\u00e3o","sequence":"additional","affiliation":[{"name":"LASOL\u2013CCQFA, Universidade Federal de Pelotas\u2014UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul","family":"Evans","sequence":"additional","affiliation":[{"name":"Centre for Synthesis and Chemical Biology, School of Chemistry University College Dublin, Dublin D04, N2E5, Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7698-8970","authenticated-orcid":false,"given":"Claudio","family":"Santi","sequence":"additional","affiliation":[{"name":"Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences University of Perugia Via del Liceo 1, 06123 Perugia, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,4,26]]},"reference":[{"key":"ref_1","unstructured":"Nicolaou, K.C., and Petasis, N.A. (1984). Selenium in Natural Products Synthesis, CIS."},{"key":"ref_2","unstructured":"Paulmier, C. (1986). 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