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Addition to “Thianthrenation-Enabled Pyrrolidin-2-yl and Tetrahydrofuran-2-yl Methylation of (Hetero)Arenes”
Organic Letters ( IF 5.2 ) Pub Date : 2023-07-19 , DOI: 10.1021/acs.orglett.3c02202
Boyu Peng , Licheng Dai , Ruzhang Liu

In the Scheme 5e of above publication, we claimed the syn addition of the Pd-heteroatom bond to the C═C double bond in both carboamination and carboalkoxylation. The reported data in the publication only supports the syn-hetereopalladation pathway for the carboamination. Occasionally, we found that the carboalkoxylations of substituted pent-4-en-1-ols 2a-2c do not afford high diastereoselectivity of products 3a3c as the syn-hetereopalladation mechanistic pathway suggests (Scheme 1a). In order to differentiate two possible syn- and anti-hetereopalladation pathways, two deuterated pent-4-en-1-ol 2d and 2e were employed for this carboalkoxylation (Scheme 1b). The obtained low diastereoselectivity in both deuterated alkenols suggests a mixed syn- and anti-hetereopalladation pathways in this reaction (Scheme 1c). (1) The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c02202. Experimental procedures, characterization data, and copies of NMR spectra (PDF) 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 1 other publications. This article has not yet been cited by other publications. This article references 1 other publications. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c02202. Experimental procedures, characterization data, and copies of NMR spectra (PDF) 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.

中文翻译:

添加“(杂)芳烃的噻嗪化吡咯烷-2-基和四氢呋喃-2-基甲基化”

在上述出版物的方案5e中,我们要求在碳胺化和碳烷氧基化中将Pd-杂原子键顺式加成到C=C双键上。该出版物中报告的数据仅支持碳胺化的顺式异钯化途径。有时,我们发现取代的 pent-4-en-1-ols 2a - 2c的烷氧基化不能提供产物3a - 3c的高非对映选择性,如顺式杂钯化机制途径所示(方案 1a)。为了区分两种可能的式和式杂钯化途径,使用两种氘化的 pent-4-en-1-ol 2d2e进行烷氧基化(方案 1b)。两种氘代烯醇中获得的低非对映选择性表明该反应中存在混合的顺式反式杂钯化途径(方案 1c)。(1) 支持信息可在 https://pubs.acs.org/doi/10.1021/acs.orglett.3c02202 免费获取。实验程序、表征数据和 NMR 谱图副本 (PDF) 大多数电子支持信息文件无需订阅 ACS 网络版即可获得。此类文件可以按文章下载用于研究用途(如果有链接到相关文章的公共使用许可证,则该许可证可能允许其他用途)。可以通过 RightsLink 许可系统提出请求,从 ACS 获得许可用于其他用途:http://pubs.acs.org/page/copyright/permissions.html。本文参考了其他 1 篇出版物。这篇文章尚未被其他出版物引用。本文参考了其他 1 篇出版物。支持信息可在 https://pubs.acs.org/doi/10.1021/acs.orglett.3c02202 免费获取。实验程序、表征数据和 NMR 谱图副本 (PDF) 大多数电子支持信息文件无需订阅 ACS 网络版即可获得。此类文件可以按文章下载用于研究用途(如果有链接到相关文章的公共使用许可证,则该许可证可能允许其他用途)。可以通过 RightsLink 许可系统提出请求,从 ACS 获得许可用于其他用途:http://pubs.acs.org/page/copyright/permissions.html。
更新日期:2023-07-19
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