{"title":"Addition to “LiOtBu-Promoted trans-Stereoselective and β-Regioselective Hydroboration of Propargyl Alcohols”","authors":"Xia Tian, Yu-Kun Zhang, Ya-Xin You, Jian-Rong Han, Qiu-Shi Cheng, Shi-Ming Fan, Di-Di Chen, Ting-Ting Wang, Shouxin Liu, Wei Su","doi":"10.1021/acs.orglett.4c04047","DOIUrl":null,"url":null,"abstract":"In the previously published communication, a paper addressing the transition-metal-free borylation of propargyl alcohols was not cited due to our concerns regarding certain analytical results presented within it. To uphold the rigor of citations, this paper is now included, (1) along with an analysis of the data that raised these concerns: In the cited study, compounds <b>2f</b> and <b>2g</b>, which were produced from γ-alkyl-substituted propargyl alcohols, were speculated to be β-regioselective and <i>trans</i>-stereoselective hydroboration products. However, based on the splitting and coupling constants observed in the <sup>1</sup>H NMR spectra, it appears that <b>2f</b> and <b>2g</b> should be classified as γ-regioselective products, and their stereoselectivity cannot be determined. Further details are provided in the Supporting Information. Additionally, according to Prof. Uchiyama’s report on the <i>trans</i>-diboration of propargyl alcohols, (2) γ-Bpin tends to undergo hydrolysis during workup, forming cyclic alkenediboronate as a product. Consequently, there are concerns regarding the description of <b>2i</b>, which retains both β- and γ-Bpin units, as a <i>trans</i>-diboration product. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c04047. Explanation of structures of <b>2f</b> and <b>2g</b> (PDF) Addition to\n“LiO<sup><i>t</i></sup>Bu-Promoted <i>trans</i>-Stereoselective and β‑Regioselective\nHydroboration of Propargyl Alcohols” <span> 4 </span><span> views </span> <span> 0 </span><span> shares </span> <span> 0 </span><span> downloads </span> Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html. This article references 2 other publications. This article has not yet been cited by other publications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04047","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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Abstract
In the previously published communication, a paper addressing the transition-metal-free borylation of propargyl alcohols was not cited due to our concerns regarding certain analytical results presented within it. To uphold the rigor of citations, this paper is now included, (1) along with an analysis of the data that raised these concerns: In the cited study, compounds 2f and 2g, which were produced from γ-alkyl-substituted propargyl alcohols, were speculated to be β-regioselective and trans-stereoselective hydroboration products. However, based on the splitting and coupling constants observed in the 1H NMR spectra, it appears that 2f and 2g should be classified as γ-regioselective products, and their stereoselectivity cannot be determined. Further details are provided in the Supporting Information. Additionally, according to Prof. Uchiyama’s report on the trans-diboration of propargyl alcohols, (2) γ-Bpin tends to undergo hydrolysis during workup, forming cyclic alkenediboronate as a product. Consequently, there are concerns regarding the description of 2i, which retains both β- and γ-Bpin units, as a trans-diboration product. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c04047. Explanation of structures of 2f and 2g (PDF) Addition to
“LiOtBu-Promoted trans-Stereoselective and β‑Regioselective
Hydroboration of Propargyl Alcohols” 4 views 0 shares 0 downloads Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html. This article references 2 other publications. This article has not yet been cited by other publications.
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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