{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T06:11:18Z","timestamp":1788675078713,"version":"build-2803163510"},"reference-count":53,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2018,5,23]],"date-time":"2018-05-23T00:00:00Z","timestamp":1527033600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21702026"],"award-info":[{"award-number":["21702026"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012226","name":"Fundamental Research Funds for the Central Universities","doi-asserted-by":"publisher","award":["N160503001, N160504001"],"award-info":[{"award-number":["N160503001, N160504001"]}],"id":[{"id":"10.13039\/501100012226","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>An efficient and practical approach towards bifunctional phosphorus phenols has been developed through a reaction of diphenylphosphine oxide and the o-quinone methides in situ generated from 2-tosylalkyl phenols under basic conditions. This protocol features simple experimental procedures under mild conditions and is easily scaled up. With this method, a variety of diarylmethyl phosphine oxides can be produced with up to 92% yield.<\/jats:p>","DOI":"10.3390\/molecules23061240","type":"journal-article","created":{"date-parts":[[2018,5,24]],"date-time":"2018-05-24T02:55:43Z","timestamp":1527130543000},"page":"1240","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Straightforward Synthesis of Bifunctional Phosphorus Phenols via Phosphination of In Situ Generated o-Quinone Methides"],"prefix":"10.3390","volume":"23","author":[{"given":"Zhangpei","family":"Chen","sequence":"first","affiliation":[{"name":"Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qinglong","family":"Shi","sequence":"additional","affiliation":[{"name":"Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gongshu","family":"Wang","sequence":"additional","affiliation":[{"name":"Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siwen","family":"Chen","sequence":"additional","affiliation":[{"name":"Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianshe","family":"Hu","sequence":"additional","affiliation":[{"name":"Center for Molecular Science and Engineering, College of Sciences, Northeastern University, Shenyang 110819, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,5,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1002\/ps.1518","article-title":"Glyphosate: A once-in-a-century herbicide","volume":"64","author":"Duke","year":"2008","journal-title":"Pest Manag. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1461","DOI":"10.1021\/ar800036s","article-title":"Palladium-Catalyzed Suzuki\u2212Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands","volume":"41","author":"Martin","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1038\/nrmicro3011","article-title":"Organophosphonates revealed: New insights into the microbial metabolism of ancient molecules","volume":"11","author":"McGrath","year":"2013","journal-title":"Nat. Rev. Microbiol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5955","DOI":"10.1021\/jm200587f","article-title":"Remarkable Potential of the \u03b1-Aminophosphonate\/Phosphinate Structural Motif in Medicinal Chemistry","volume":"54","author":"Mucha","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1629","DOI":"10.1021\/cr030026j","article-title":"Mixed Phosphine\u2212Phosphine Oxide Ligands","volume":"104","author":"Grushin","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_6","first-page":"29","article-title":"Chiral Phosphorus Ligands with Interesting Properties and Practical Applications","volume":"36","author":"Lam","year":"2011","journal-title":"Top. Organomet. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"630","DOI":"10.1039\/B517100H","article-title":"Catalytic asymmetric synthesis of \u03b1- and \u03b2-amino phosphonic acid derivatives","volume":"35","author":"Ma","year":"2006","journal-title":"Chem. Soc. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"11892","DOI":"10.1021\/ja073992i","article-title":"Synthesis of Tamiflu and its Phosphonate Congeners Possessing Potent Anti-Influenza Activity","volume":"129","author":"Shie","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","first-page":"1","article-title":"Phosphines and related P\u2013C-bonded Compounds","volume":"41","author":"Allen","year":"2012","journal-title":"Organophosphorus Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"6491","DOI":"10.1002\/anie.200461312","article-title":"Stereospecific, Enantioselective Allylation of \u03b1-Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral-Coordinate Organocatalysts","volume":"43","author":"Ogawa","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5704","DOI":"10.1021\/acs.chemrev.6b00536","article-title":"Phosphonate Biochemistry","volume":"117","author":"Horsman","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2391","DOI":"10.1016\/j.tetasy.2005.06.021","article-title":"Asymmetric ring opening of meso-epoxides catalyzed by the chiral phosphine oxide BINAPO","volume":"16","author":"Tokuoka","year":"2005","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3633","DOI":"10.1016\/j.tet.2012.02.078","article-title":"The synthesis of phosphine oxide-linked bis(oxazoline) ligands and their application in asymmetric allylic alkylation","volume":"68","author":"Jin","year":"2012","journal-title":"Tetrahedron"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"949","DOI":"10.1016\/j.steroids.2006.07.003","article-title":"Novel phosphorus-containing 17\u03b2-side chain mifepristone analogues as progesterone receptor antagonists","volume":"71","author":"Jiang","year":"2006","journal-title":"Steroids"},{"key":"ref_15","unstructured":"Harada, T., Yamanaka, Y., Matsushita, Y., and Fukushima, K. (2011). Flame Retardant Resin Composition and Molded Product. (EP2681281A12014)."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1195","DOI":"10.1002\/adsc.200800131","article-title":"Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines","volume":"350","author":"Merino","year":"2008","journal-title":"Adv. Synth. Catal."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2672","DOI":"10.1021\/cr800315j","article-title":"Direct Phosphonylation of Aromatic Azaheterocycles","volume":"109","author":"Stevens","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1002\/chem.200902634","article-title":"Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds","volume":"16","author":"Albrecht","year":"2010","journal-title":"Chem. Eur. J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"7981","DOI":"10.1021\/cr2002646","article-title":"Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group","volume":"111","author":"Demmer","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2095","DOI":"10.1039\/C1CS15247E","article-title":"Recent developments in metal catalyzed asymmetric addition of phosphorus nucleophiles","volume":"41","author":"Zhao","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1021\/cr00044a004","article-title":"Michaelis-Arbuzov rearrangement","volume":"81","author":"Bhattacharya","year":"1981","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1270","DOI":"10.1021\/ol1029436","article-title":"Lewis Acid-Mediated Michaelis\u2212Arbuzov Reaction at Room Temperature: A Facile Preparation of Arylmethyl\/Heteroarylmethyl Phosphonates","volume":"13","author":"Rajeshwaran","year":"2011","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"944","DOI":"10.1002\/ejoc.201201352","article-title":"FeCl3-Mediated Arylation of \u03b1-Hydroxyphosphonates with Unactivated Arenes: Pseudo-Umpolung in Allylic Phosphonates","volume":"2013","author":"Pallikonda","year":"2013","journal-title":"Eur. J. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1021\/ol403124g","article-title":"Palladium-Catalyzed \u03b1-Arylation of Benzylic Phosphine Oxides","volume":"16","author":"Montel","year":"2014","journal-title":"Org. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5550","DOI":"10.1039\/C6OB00289G","article-title":"N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: An atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates","volume":"14","author":"Arde","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"958","DOI":"10.1021\/acs.orglett.7b00261","article-title":"Synthesis of Diaryl Diazaphosphonates via 1,6-Hydrophosphonylation of p-Quinone Methides with N-Heterocyclic Phosphine\u2013Thioureas","volume":"19","author":"Molleti","year":"2017","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"5988","DOI":"10.1021\/acs.orglett.7b03019","article-title":"Organocatalytic Phosphonylation of in situ Formed o-Quinone Methides","volume":"19","author":"Huang","year":"2017","journal-title":"Org. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Chatt, J., and Heaton, B.T. (1968). The hydrolysis of monochlorophosphine and monochloroarsine complexes of platinum (II): Bridging phosphinato- and arsinato-groups. J. Chem. Soc. A, 2745\u20132757.","DOI":"10.1039\/j19680002745"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1080\/10426500490256989","article-title":"Chemo- and stereoselective addition of diorganylphosphine oxides to \u03b1,\u03b2-ethylenic aldehydes","volume":"179","author":"Ivanova","year":"2004","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5367","DOI":"10.1016\/S0040-4020(02)00496-9","article-title":"o-Quinone methides: Intermediates underdeveloped and underutilized in organic synthesis","volume":"58","author":"Pettus","year":"2002","journal-title":"Tetrahedron"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"9160","DOI":"10.1002\/chem.201200619","article-title":"ortho-Quinone Methides in Natural Product Synthesis","volume":"18","author":"Willis","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4524","DOI":"10.1021\/ja00167a060","article-title":"Synthesis and chemistry of a quinone methide model for anthracycline antitumor antibiotics","volume":"112","author":"Angle","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3488","DOI":"10.1039\/b508972g","article-title":"A new and efficient method for o-quinone methide intermediate generation: Application to the biomimetic synthesis of the benzopyran derived natural products (\u00b1)-lucidene and (\u00b1)-alboatrin","volume":"3","author":"Rodriguez","year":"2005","journal-title":"Org. Biomol. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"11940","DOI":"10.1021\/ja062948k","article-title":"Substituents on Quinone Methides Strongly Modulate Formation and Stability of Their Nucleophilic Adducts","volume":"128","author":"Weinert","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2815","DOI":"10.1039\/b806593d","article-title":"Generation and hetero-Diels\u2013Alder reactions of an o-quinone methide under mild, anionic conditions: Rapid synthesis of mono-benzannelated spiroketals","volume":"6","author":"Bray","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Bray, C.D. (2008). An Approach to Benzannelated [5,6]-Spiroketals. Synlett, 2500\u20132502.","DOI":"10.1055\/s-2008-1078057"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"11892","DOI":"10.1021\/ja9031924","article-title":"Photochemical Generation and the Reactivity of o-Naphthoquinone Methides in Aqueous Solutions","volume":"131","author":"Arumugam","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1139\/V10-102","article-title":"Competing photodehydration and excited-state intramolecular proton transfer (ESIPT) in adamantyl derivatives of 2-phenylphenols","volume":"89","author":"Cindro","year":"2011","journal-title":"Can. J. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"5500","DOI":"10.1021\/ol2022214","article-title":"Total Synthesis and Repudiation of the Helianane Family","volume":"13","author":"Green","year":"2011","journal-title":"Org. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"9210","DOI":"10.1021\/jo201789k","article-title":"Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis","volume":"76","author":"Pathak","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3096","DOI":"10.1021\/jo102531f","article-title":"Quinone Methide Generation via Photoinduced Electron Transfer","volume":"76","author":"Percivalle","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3904","DOI":"10.1016\/j.tet.2011.03.059","article-title":"Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides","volume":"67","author":"Radomkit","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1357","DOI":"10.1021\/ja210655g","article-title":"Simultaneous Synthesis of Both Rings of Chromenes via a Benzannulation\/o-Quinone Methide Formation\/Electrocyclization Cascade","volume":"134","author":"Majumdar","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1660","DOI":"10.1039\/c3cc37800d","article-title":"A mild method for generation of o-quinone methides under basic conditions. The facile synthesis of trans-2,3-dihydrobenzofurans","volume":"49","author":"Chen","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1002\/cjoc.201400463","article-title":"A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols","volume":"32","author":"Wu","year":"2014","journal-title":"Chin. J. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"6134","DOI":"10.1021\/acs.orglett.5b03148","article-title":"C\u2013H Oxidation\/Michael Addition\/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes","volume":"17","author":"Wu","year":"2015","journal-title":"Org. Lett."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4334","DOI":"10.1016\/j.tetlet.2015.05.076","article-title":"Enantioselective synthesis of functionalized 2-amino-4H-chromenes via the o-quinone methides generated from 2-(1-tosylalkyl)phenols","volume":"56","author":"Wu","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"4522","DOI":"10.1002\/anie.201409894","article-title":"Formal Asymmetric Catalytic Thiolation with a Bifunctional Catalyst at a Water\u2013Oil Interface: Synthesis of Benzyl Thiols","volume":"54","author":"Guo","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1135","DOI":"10.1016\/j.tetlet.2015.01.078","article-title":"Direct amination of 2-(1-tosylalkyl)phenols with aqueous ammonia: A metal-free synthesis of primary amines","volume":"56","author":"Wu","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"4006","DOI":"10.1002\/anie.201700437","article-title":"Regioselective \u03b1-Addition of Deconjugated Butenolides: Enantioselective Synthesis of Dihydrocoumarins","volume":"56","author":"Wu","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"3531","DOI":"10.1039\/C7CC01072A","article-title":"Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols","volume":"53","author":"Zhou","year":"2017","journal-title":"Chem. Commun."},{"key":"ref_52","unstructured":"Nakamoto, Y., Hirotsu, K., and Yamada, S. (2013). Phosphorus-Containing Curable Resin Compositions and Cured Products Thereof with Excellent Fire and Hydrolysis Resistance. (JP2013095818)."},{"key":"ref_53","unstructured":"Nakamoto, Y., Hirotsu, K., and Yamada, S. (2012). Diarylphosphine Oxides Bearing Oxyphenyl Groups, Diarylphosphoryl Alcohols as Their Intermediates, Manufacture of Them and Intermediates, Fireproofing Agents Containing Them, and Monomers for Fire-Resistant Resins. (WO2012039473)."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/6\/1240\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:05:35Z","timestamp":1760195135000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/6\/1240"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,23]]},"references-count":53,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2018,6]]}},"alternative-id":["molecules23061240"],"URL":"https:\/\/doi.org\/10.3390\/molecules23061240","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,23]]}}}