Xiaoyu Yan, Shangyuan Li, Mengcheng Zhang, Jing Yu, Xiantao Ma
{"title":"Exclusive Markovnikov Synthesis of Tertiary Phosphine Sulfides from Secondary Phosphine Oxides, S8, and Alkenes","authors":"Xiaoyu Yan, Shangyuan Li, Mengcheng Zhang, Jing Yu, Xiantao Ma","doi":"10.1021/acs.orglett.6c02729","DOIUrl":null,"url":null,"abstract":"<p>A novel one-pot synthesis of valuable\r\ntertiary phosphine sulfides\r\nfrom secondary phosphine oxides, elemental sulfur (S<sub>8</sub>),\r\nand alkenes has been developed, featuring exclusive Markovnikov selectivity.\r\nThis method offers significant advantages in the one-pot construction\r\nof three new C–P(═S) chemical bonds. It exhibits a broad\r\nsubstrate scope, accommodating mono-, di-, tri-, and even tetrasubstituted\r\nalkenes, and can be readily scaled up to a gram scale. Mechanistic\r\ninvestigations revealed two key steps: (1) an unexpected disproportionation\r\nprocess that cleaves the robust P═O bonds of dialkylphosphine\r\noxides and (2) the Markovnikov hydrophosphination of alkenes with\r\nan <em>in situ</em> generated dialkylphosphine intermediate.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 29","pages":"9542–9546"},"PeriodicalIF":4.7000,"publicationDate":"2026-07-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.6c02729","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/7/13 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel one-pot synthesis of valuable
tertiary phosphine sulfides
from secondary phosphine oxides, elemental sulfur (S8),
and alkenes has been developed, featuring exclusive Markovnikov selectivity.
This method offers significant advantages in the one-pot construction
of three new C–P(═S) chemical bonds. It exhibits a broad
substrate scope, accommodating mono-, di-, tri-, and even tetrasubstituted
alkenes, and can be readily scaled up to a gram scale. Mechanistic
investigations revealed two key steps: (1) an unexpected disproportionation
process that cleaves the robust P═O bonds of dialkylphosphine
oxides and (2) the Markovnikov hydrophosphination of alkenes with
an in situ generated dialkylphosphine intermediate.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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