{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,12]],"date-time":"2026-06-12T07:02:11Z","timestamp":1781247731127,"version":"3.54.1"},"reference-count":45,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,22]],"date-time":"2021-02-22T00:00:00Z","timestamp":1613952000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Science and Technology in Taiwan","award":["MOST 109-2113-M-027-003"],"award-info":[{"award-number":["MOST 109-2113-M-027-003"]}]},{"name":"university joint grants","award":["NTUT-CGMH-109-07"],"award-info":[{"award-number":["NTUT-CGMH-109-07"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Phospha-Michael addition, which is the addition reaction of a phosphorus-based nucleophile to an acceptor-substituted unsaturated bond, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds, since many different electrophiles and P nucleophiles can be combined with each other. This offers the possibility to access many diversely functionalized products. In this work, two kinds of basic pyridine-based organo-catalysts were used to efficiently catalyze phospha-Michael addition reactions, the 4-N,N-dimethylaminopyridinium saccharinate (DMAP\u00b7Hsac) salt and a fluorous long-chained pyridine (4-Rf-CH2OCH2-py, where Rf = C11F23). These catalysts have been synthesized and characterized by Lu\u2019s group. The phospha-Michael addition of diisopropyl, dimethyl or triethyl phosphites to \u03b1, \u03b2-unsaturated malonates in the presence of those catalysts showed very good reactivity with high yield at 80\u2013100 \u00b0C in 1\u20134.5 h with high catalytic recovery and reusability. With regard to significant catalytic recovery, sometimes more than eight cycles were observed for DMAP\u00b7Hsac adduct by using non-polar solvents (e.g., ether) to precipitate out the catalyst. In the case of the fluorous long-chained pyridine, the thermomorphic method was used to efficiently recover the catalyst for eight cycles in all the reactions. Thus, the easy separation of the catalysts from the products revealed the outstanding efficacy of our systems. To our knowledge, these are good examples of the application of recoverable organo-catalysts to the DMAP\u00b7Hsac adduct by using non-polar solvent and a fluorous long-chained pyridine under the thermomorphic mode in phospha-Michael addition reactions.<\/jats:p>","DOI":"10.3390\/molecules26041159","type":"journal-article","created":{"date-parts":[[2021,2,22]],"date-time":"2021-02-22T20:42:51Z","timestamp":1614026571000},"page":"1159","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Recoverable Phospha-Michael Additions Catalyzed by a 4-N,N-Dimethylaminopyridinium Saccharinate Salt or a Fluorous Long-Chained Pyridine: Two Types of Reusable Base Catalysts"],"prefix":"10.3390","volume":"26","author":[{"given":"Eskedar","family":"Tessema","sequence":"first","affiliation":[{"name":"Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8444-5776","authenticated-orcid":false,"given":"Vijayanath","family":"Elakkat","sequence":"additional","affiliation":[{"name":"Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chiao-Fan","family":"Chiu","sequence":"additional","affiliation":[{"name":"Department of Pediatrics, Linkou Medical Center, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan"},{"name":"Graduate Institute of Clinical Medical Sciences, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jing-Hung","family":"Zheng","sequence":"additional","affiliation":[{"name":"Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ka Long","family":"Chan","sequence":"additional","affiliation":[{"name":"Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8386-3965","authenticated-orcid":false,"given":"Chia-Rui","family":"Shen","sequence":"additional","affiliation":[{"name":"Department of Medical Biotechnology and Laboratory Sciences, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan"},{"name":"Department of Ophthalmology, Linkou Medical Center, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Cincinnati, Cincinnati, OH 45221-0172, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Norman","family":"Lu","sequence":"additional","affiliation":[{"name":"Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan"},{"name":"Development Center for Smart Textile, National Taipei University of Technology, Taipei 106, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,22]]},"reference":[{"key":"ref_1","unstructured":"Anastas, P.T., and Williamson, T.C. 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