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Correction to “Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI”
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-08-04 , DOI: 10.1021/jacs.2c07580 He Liu , Jian Wu , Yuxuan Jin , Xuebing Leng , Qilong Shen
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-08-04 , DOI: 10.1021/jacs.2c07580 He Liu , Jian Wu , Yuxuan Jin , Xuebing Leng , Qilong Shen
Page 14368. Scheme 1 in the published work should be replaced with the version below, in which part E has been added. The following sentence should be added to the text discussion of Scheme 1, at the end of the paragraph that begins, “To elucidate the structure of the observed [CF3Cu] species, ...”: Grushin and co-workers prepared and characterized a ligandless CuCF3 (−26.9 ppm in DMF) and studied the mechanism of the reaction of the ligandless CuCF3 with aryl iodides (Scheme 1E).19b Page 14370. The following sentences should be added on at the end of the paragraph in which Figure 2 is cited: X-ray diffraction studies of the single crystals of both complexes 1b and 1c show that there are significant static disorders in both structures. The crystals of complex 1b exist as a mixture of two species, [Cu(CF3)(Cl)]− and [Cu(CF3)2]−, while the crystals of complex 1c are a mixture of three species, [Cu(CF3)(I)]−, [Cu(CF3)2]−, and [CuI2]−. The structures of complexes 1b and 1c were tentatively assigned as [Cu(CF3)(Cl)]− and [Cu(CF3)(I)]−, since the unit-cell parameters of the crystal lattices of [Cu(CF3)2]− and [CuI2]− are different from those of complexes 1b and 1c. The quality of the X-ray diffraction data was not high enough to obtain detailed structural information on both complexes. The Cu–CF3 bond distances in both structures were not accurate due to the disorder. Page 14374. The sentence beginning “It was found that the reaction occurred so fast...”, in which Scheme 5, eq 1, is cited, should be replaced by the following: It was found that the reaction occurred so fast that [nBu4N]+[CuI2]−1d was generated after the mixture of CuI and nBu4NI was shaken in CH2Cl2 for 30 s and further violently stirred for 10 min, and complex 1d was isolated as a gray solid in 96% yield after evaporation of the solvent (Scheme 5, eq 1). A solution of equimolar, freshly prepared [Cu(CF3)2]− and [nBu4N]+[CuI2]− in DMF reacted quickly at room temperature to generate [Cu(CF3)(I)]−, with a conversion of 40% after 10 min (Scheme 5, eq 2). Page 14378. In ref 19, the original citation should be identified as part (a), with the new text and new ref 19b, given below as ref (1), added, as follows: (19) (a) Martínez de Salinas, S.; Mudarra, Á. L.; Odena, C.; MartínezBelmonte, M.; Benet-Buchholz, J.; Maseras, F.; Pérez-Temprano, M. H. Exploring the Role of Coinage Metalates in Trifluoromethylation: A Combined Experimental and Theoretical Study. Chem. - Eur. J.2019, 25, 9390–9394. (b) For mechanistic investigation of a ligandless CuCF3 with ArI, see: Konovalov, A. I.; Lishchynskyi, A.; Grushin, V. V. Mechanism of Trifluoromethylation of Aryl Halides with CuCF3 and the Ortho Effect. J. Am. Chem. Soc.2014, 136, 13410–13425. Supporting Information. The procedure for the preparation of [nBu4N]+[CuI2]− on page S5 and the procedure for generation of [Cu(CF3)(I)]− from the reaction of [Cu(CF3)2]− with [nBu4N]+[CuI2]− on page S10 have been updated. The complete corrected Supporting Information file is provided herein. The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c07580. Experimental details and kinetic profiles; 1H, 19F, and 13C NMR spectra of 1a–c and 2a–l (corrected) (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/jacs.2c07580. Experimental details and kinetic profiles; 1H, 19F, and 13C NMR spectra of 1a–c and 2a–l (corrected) (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：
更正“对铜介导的芳基卤化物三氟甲基化的机理洞察：CuI 的作用”
第14368页。已发表作品中的方案1应替换为以下版本，其中添加了E部分。以下句子应添加到方案 1 的文本讨论中，在开始的段落末尾，“为了阐明观察到的 [CF 3 Cu] 物种的结构，......”：Grushin 和同事准备并表征了无配体 CuCF 3（DMF 中 -26.9 ppm）并研究了无配体 CuCF 3与芳基碘化物的反应机理（方案 1E）。19b第 14370 页。应在引用图 2 的段落末尾添加以下句子： 配合物1b和1c的单晶的 X 射线衍射研究表明两种结构都存在显着的静态障碍。配合物1b的晶体以两种物质的混合物存在，[Cu(CF 3 )(Cl)] -和 [Cu(CF 3 ) 2 ] -，而配合物1c的晶体是三种物质的混合物，[Cu (CF 3 )(I)] -、[Cu(CF 3 ) 2 ] -和[CuI 2 ] -。配合物1b和1c的结构暂定为[Cu(CF 3 )(Cl)] -和[Cu(CF 3)(I)] - ，因为[Cu(CF 3 ) 2 ] -和[CuI 2 ] -的晶格的晶胞参数不同于配合物1b和1c的晶胞参数。X 射线衍射数据的质量不足以获得两种配合物的详细结构信息。由于无序，两种结构中的 Cu-CF 3键距离都不准确。第 14374 页。 引用方案 5 等式 1 的以“发现反应发生得如此之快...”开头的句子应替换为：发现反应发生得如此之快以至于 [ n卜4N] + [CuI 2 ] -将CuI和n Bu 4 NI的混合物在CH 2 Cl 2中振荡30 s，再剧烈搅拌10 min后生成N] + [CuI 2 ] - 1d ，在96中分离出复合物1d，为灰色固体溶剂蒸发后的％产率（方案 5，eq 1）。等摩尔的新制备的[Cu(CF 3 ) 2 ] -和[ n Bu 4 N] + [CuI 2 ] -在DMF中的溶液在室温下快速反应生成[Cu(CF 3 )(I)]−，10 分钟后转化率为 40%（方案 5，eq 2）。第 14378 页。在参考文献 19 中，原始引文应标识为 (a) 部分，新文本和新参考文献 19b，如下文参考文献 (1)，添加如下： (19) (a) Martínez de Salinas , S.; 穆达拉，Á. L.; 奥德纳，C。马丁内斯贝尔蒙特，M.；贝内特-布赫霍尔兹，J.；马塞拉斯，F。Pérez-Temprano, MH 探索造币金属酸盐在三氟甲基化中的作用：一项结合实验和理论的研究。化学。- 欧元。J. 2019，25，9390–9394。_ _ (b) 无配体 CuCF 3与 ArI 的机理研究，参见：Konovalov，AI；利什琴斯基，A.；Grushin, VV 芳基卤化物与 CuCF 3的三氟甲基化机理和邻位效应。J.上午。化学。社会党。2014 年，136，13410–13425。支持信息。[ n Bu 4 N] + [CuI 2 ] -的制备步骤（第 S5 页）和 [Cu(CF 3 )(I)] -由 [Cu(CF 3 ) 2 ]的反应生成的步骤- [ n Bu 4 N] + [CuI 2 ] -第 S10 页上的已更新。此处提供了完整的更正支持信息文件。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c07580 免费获得。实验细节和动力学曲线；1a-c和2a-l的1 H、19 F 和13 C NMR 光谱（已更正）（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以供研究使用（如果有与相关文章链接的公共使用许可，则该许可可能允许其他用途）。可通过 RightsLink 许可系统请求从 ACS 获得其他用途的许可：http://pubs.acs.org/page/copyright/permissions.html。本文参考了 1 篇其他出版物。这篇文章尚未被其他出版物引用。本文参考了 1 篇其他出版物。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c07580 免费获得。实验细节和动力学曲线；1 H、19 F 和131a–c和2a–l的 C NMR 光谱（已修正）(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以供研究使用（如果有与相关文章链接的公共使用许可，则该许可可能允许其他用途）。可通过 RightsLink 许可系统请求从 ACS 获得其他用途的许可：http://pubs.acs.org/page/copyright/permissions.html。
更新日期：2022-08-04
中文翻译：
更正“对铜介导的芳基卤化物三氟甲基化的机理洞察：CuI 的作用”
第14368页。已发表作品中的方案1应替换为以下版本，其中添加了E部分。以下句子应添加到方案 1 的文本讨论中，在开始的段落末尾，“为了阐明观察到的 [CF 3 Cu] 物种的结构，......”：Grushin 和同事准备并表征了无配体 CuCF 3（DMF 中 -26.9 ppm）并研究了无配体 CuCF 3与芳基碘化物的反应机理（方案 1E）。19b第 14370 页。应在引用图 2 的段落末尾添加以下句子： 配合物1b和1c的单晶的 X 射线衍射研究表明两种结构都存在显着的静态障碍。配合物1b的晶体以两种物质的混合物存在，[Cu(CF 3 )(Cl)] -和 [Cu(CF 3 ) 2 ] -，而配合物1c的晶体是三种物质的混合物，[Cu (CF 3 )(I)] -、[Cu(CF 3 ) 2 ] -和[CuI 2 ] -。配合物1b和1c的结构暂定为[Cu(CF 3 )(Cl)] -和[Cu(CF 3)(I)] - ，因为[Cu(CF 3 ) 2 ] -和[CuI 2 ] -的晶格的晶胞参数不同于配合物1b和1c的晶胞参数。X 射线衍射数据的质量不足以获得两种配合物的详细结构信息。由于无序，两种结构中的 Cu-CF 3键距离都不准确。第 14374 页。 引用方案 5 等式 1 的以“发现反应发生得如此之快...”开头的句子应替换为：发现反应发生得如此之快以至于 [ n卜4N] + [CuI 2 ] -将CuI和n Bu 4 NI的混合物在CH 2 Cl 2中振荡30 s，再剧烈搅拌10 min后生成N] + [CuI 2 ] - 1d ，在96中分离出复合物1d，为灰色固体溶剂蒸发后的％产率（方案 5，eq 1）。等摩尔的新制备的[Cu(CF 3 ) 2 ] -和[ n Bu 4 N] + [CuI 2 ] -在DMF中的溶液在室温下快速反应生成[Cu(CF 3 )(I)]−，10 分钟后转化率为 40%（方案 5，eq 2）。第 14378 页。在参考文献 19 中，原始引文应标识为 (a) 部分，新文本和新参考文献 19b，如下文参考文献 (1)，添加如下： (19) (a) Martínez de Salinas , S.; 穆达拉，Á. L.; 奥德纳，C。马丁内斯贝尔蒙特，M.；贝内特-布赫霍尔兹，J.；马塞拉斯，F。Pérez-Temprano, MH 探索造币金属酸盐在三氟甲基化中的作用：一项结合实验和理论的研究。化学。- 欧元。J. 2019，25，9390–9394。_ _ (b) 无配体 CuCF 3与 ArI 的机理研究，参见：Konovalov，AI；利什琴斯基，A.；Grushin, VV 芳基卤化物与 CuCF 3的三氟甲基化机理和邻位效应。J.上午。化学。社会党。2014 年，136，13410–13425。支持信息。[ n Bu 4 N] + [CuI 2 ] -的制备步骤（第 S5 页）和 [Cu(CF 3 )(I)] -由 [Cu(CF 3 ) 2 ]的反应生成的步骤- [ n Bu 4 N] + [CuI 2 ] -第 S10 页上的已更新。此处提供了完整的更正支持信息文件。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c07580 免费获得。实验细节和动力学曲线；1a-c和2a-l的1 H、19 F 和13 C NMR 光谱（已更正）（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以供研究使用（如果有与相关文章链接的公共使用许可，则该许可可能允许其他用途）。可通过 RightsLink 许可系统请求从 ACS 获得其他用途的许可：http://pubs.acs.org/page/copyright/permissions.html。本文参考了 1 篇其他出版物。这篇文章尚未被其他出版物引用。本文参考了 1 篇其他出版物。支持信息可在 https://pubs.acs.org/doi/10.1021/jacs.2c07580 免费获得。实验细节和动力学曲线；1 H、19 F 和131a–c和2a–l的 C NMR 光谱（已修正）(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以供研究使用（如果有与相关文章链接的公共使用许可，则该许可可能允许其他用途）。可通过 RightsLink 许可系统请求从 ACS 获得其他用途的许可：http://pubs.acs.org/page/copyright/permissions.html。
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