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Data revision requests:
数据修订请求:

1. Please reformat the Data Availability Statement so it is in the ACS Research Data Policy Style. https://publish.acs.org/publish/data_policy for more information.
1. 请重新设置数据可用性声明的格式,使其符合 ACS Research 数据政策格式。https://publish.acs.org/publish/data_policy 了解更多信息。

ASSOCIATED CONTENT:

Data Availability Statement
数据可用性声明

The data underlying this study are available in the published article and its Supporting Information.
本研究的基础数据可在已发表的文章及其支持信息中找到。

Supporting Information Statement
支持信息声明

General experimental procedures, X-ray crystallographic data, and NMR spectra is available free of charge via the Internet at http://pubs.acs.org.
一般实验程序、X 射线晶体学数据和 NMR 波谱可通过 http://pubs.acs.org 的互联网免费获得。

2. For light-promoted reactions, report the light source in detail (manufacturer and model, wavelength of peak intensity or broadband source, and available information about the spectral distribution and intensity); the material of the irradiation vessel if other than borosilicate glass; and the use of filters if any.
2. 对于光促进反应,详细报告光源(制造商和型号、峰值强度或宽带光源的波长,以及有关光谱分布和强度的可用信息);辐照容器的材料(如果不是硼硅酸盐玻璃);以及过滤器的使用(如果有)。

3. The reported yield in the (Table 2) differs from the reported yield in the Experimental Section (page no S4) for compound(s): 7.
3. 对于化合物,(表 2)中报告的产量与实验部分(第 S4 页)中报告的产量不同: 7.

4. Please use 13C{1H} braces when reporting proton-decoupled carbon data in the experimental details. A typical example is shown below:                                                                                        
4. 在实验细节中报告质子解耦碳数据时,请使用 13C{1H} 大括号。一个典型的例子如下所示:

13C{1H} NMR (126 MHz, CDCl3) δ 144.0, 134.6, 128.5, 127.6, 125.9, 118.4, 73.4.
13C{1H} 核磁共振 (126 MHz, CDCl3) δ 144.0、134.6、128.5、127.6、125.9、118.4、73.4。

5. Please use 13C{1H} for proton-decoupled carbon data on each NMR spectrum in ESI.
5. 请使用 13C{1H} 获取 ESI 中每个 NMR 谱图的质子解耦碳数据。

6. Please identify the solvent on each NMR spectrum in ESI.
6. 请在 ESI 中识别每个 NMR 谱图上的溶剂。

Please identify the NMR Hz on each NMR spectrum in ESI.
请识别 ESI 中每个 NMR 谱图上的 NMR Hz。

8. When flash chromatography is used for product purification, the solvent should be identified for each compound.
8. 当使用快速色谱法进行产品纯化时,应确定每种化合物的溶剂。

9. Please include a text description of the instrumentation used for the crystal measurement.
9. 请附上用于晶体测量的仪器的文本描述。

10. Please include a text description of the sample preparation (i.e., solvent system and method for crystal growth).
10. 请包括样品制备的文本描述(即溶剂系统和晶体生长方法)。

11. Please include a thermal ellipsoid plot for each crystal structure, preferably full-page size, in the Supporting Information.
11. 请在支持信息中包括每种晶体结构的热椭球体图,最好是整页大小。

12. Please indicate the ellipsoid contour % probability levels in the caption for the image of the structure.
12. 请在结构图像的标题中注明椭球等值线 % 概率水平。

13. Please reformat and provide the HPLC data for compounds: 36-41 to conform to ACS Guide format. A typical example is: HPLC (OD-H, ethanol/n-hexane = 10/90, flow rate = 1.0 mL/min, l = 254 nm) tR = 18.9 min (major), 20.3 min (minor).
13. 请重新格式化并提供化合物的 HPLC 数据:36-41,以符合 ACS 指南格式。典型示例为:HPLC(OD-H,乙醇/正己烷 = 10/90,流速 = 1.0 mL/min,l = 254 nm)tR = 18.9 min(主要),20.3 min(次要)。

14. Please include a structure on the 1H NMR spectra for compound(s):4.
14. 请在 1H NMR 波谱上包括化合物的结构:4。

15. Please re-position the structures the NMR spectra for compounds: 28, 30 so they are not overlapping any details.
15. 请重新定位化合物的 NMR 波谱结构:28、30,这样它们就不会重叠任何细节。

16. The HRMS mass does not match the reported formula for compound(s): 36.
16. HRMS 质量数与报告的化合物公式不匹配:36。

17. The HRMS analysis is not within the 10 ppm acceptable error for compound(s):39.
17. HRMS 分析未在化合物的 10 ppm 可接受误差范围内:39。

18. Kindly address the query given by Reviewer 1.
18. 请回答审稿人 1 给出的问题。

1) Clean up the NMR spectra corresponding to the following figures in the Supporting Information: S11, S19, S22, S26, S28, S30, S33, S36, S56, S59, S61, S70, S72, S74, S76, and S78.
1) 清理与支持信息中以下数字相对应的 NMR 波谱:S11、S19、S22、S26、S28、S30、S33、S36、S56、S59、S61、S70、S72、S74、S76 和 S78。

2) In some spectra, compound structures appear multiple times. Kindly review and remove any duplicate structures.
2) 在某些光谱中,化合物结构出现多次。请检查并删除任何重复的结构。

3) Also, check for any instances where compound structures are overlapping with NMR peaks and adjust accordingly.
3) 此外,检查化合物结构与 NMR 峰重叠的任何情况,并进行相应调整。

19. Kindly address the query given by Reviewer 3.
19. 请回答审稿人 3 给出的问题。

1. The H NMR spectra of compounds 3a, 4, 7, 17, 18, 19, and 39 show significant peaks of water or impurities, which require further purification. In addition, the integral values in the H NMR spectra of almost all products are integers, which might be intentional.
1. 化合物 3a、4、7、17、18、19 和 39 的 H NMR 波谱显示明显的水或杂质峰,需要进一步纯化。此外,几乎所有产品的 H NMR 波谱中的积分值都是整数,这可能是有意为之。

20. Please indicate the source and/or preparation for compound(s) 1 and 2:
20. 请说明化合物 1 和 2 的来源和/或制备方法:

**For new compounds, full characterization data should be provided.
**对于新化合物,应提供完整的表征数据。

**For known compounds synthesized by published methods, please include the reference and submit one or more of the following for purity documentation (1H NMR spectrum, 13C NMR spectrum, elemental analysis, GC or HPLC). If new data is generated in the process of synthesizing this compound (for example recording a melting point or additional 2D spectra not included with the original reference), please include it the experimental details and identify it as new data
**对于通过已发表方法合成的已知化合物,请包括参考文献并提交以下一项或多项以获得纯度文件(1H NMR 谱、13C NMR 谱、元素分析、GC 或 HPLC)。如果在合成该化合物的过程中产生了新数据(例如,记录原始参考文献中未包含的熔点或其他 2D 谱图),请将其包含实验详细信息,并将其标识为新数据

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ACS Publications 有一个安全注意事项指南,即“作者必须强调与报告的工作相关的任何意外、新的和/或重大的危险或风险。这些危害或风险需要采取预防措施,而不是通常预期存在于实验室环境中的措施。要求所有作者在他们的手稿中包括一份安全声明,描述这些危害和风险,以便其他人可以安全地复制或构建他们的作品。有关准备对账单的详细信息,请参阅 https://pubs.acs.org/pb-assets/documents/policy/Safety_Statement_Style_Sheet.pdf。

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资金来源:作者需要报告与本手稿相关的所有资金来源和资助/奖励编号。确认与本手稿相关的所有作者的所有资金来源都包含在提交表格和手稿文件中,以满足此要求。有关完整说明,请参阅 http://pubs.acs.org/page/4authors/funder_options.html。

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ACS Publications uses Crossref Similarity Check Powered by iThenticate to detect instances of similarity in submitted manuscripts. In publishing only original research, ACS is committed to deterring plagiarism, including self-plagiarism. Your manuscript may be screened for similarity to published material.
ACS Publications 使用由 iThenticate 提供支持的 Crossref 相似性检查来检测已提交手稿中的相似性实例。ACS 仅发表原创研究,致力于阻止剽窃,包括自我剽窃。您的手稿可能会被筛选为与已发表材料的相似性。

Reviewer: 1
评论者: 1

Recommendation: Publish in The Journal of Organic Chemistry after minor revisions.
建议:在稍作修改后在 The Journal of Organic Chemistry 上发表。

Comments:

In this manuscript, Xiao and colleagues present a methodology for the synthesis of chiral imidazolidines represent essential structural motifs in natural products, ligands, and catalysts. A broad range of substrates was found to be compatible, delivering the chiral imidazolidines in good yields with high diastereoselectivity. The reaction mechanism was investigated through radical trapping experiments. The developed approach is conducted under mild reaction conditions and shows excellent tolerance towards various functional groups. However, I recommend its publication in this journal after the following comments have been addressed:
在这份手稿中,Xiao 及其同事提出了一种合成手性咪唑烷胺的方法,该方法代表了天然产物、配体和催化剂中的基本结构基序。发现多种底物是相容的,以良好的产量和高非对映选择性提供手性咪唑烷。通过自由基捕获实验研究了反应机理。开发的方法是在温和的反应条件下进行的,并且对各种官能团表现出优异的耐受性。但是,我建议在解决以下评论后在本期刊上发表它:

1) Many seminal reviews (like Chem. Rev. 2006, 106, 4484-4517 and other) and recent work on azomethine ylides (AMY) and not cited. Like new ways (electrochemical, photochemical) generation of AMY also should be stated.
1) 许多开创性的评论(如 Chem. Rev. 2006, 106, 4484-4517 等)和关于偶氮甲嘧啶酰化物 (AMY) 的最新工作,但未被引用。像新方法(电化学、光化学)产生 AMY 也应该说明。

2) Clean up the NMR spectra corresponding to the following figures in the Supporting Information: S11, S19, S22, S26, S28, S30, S33, S36, S56, S59, S61, S70, S72, S74, S76, and S78.
2) 清理与支持信息中以下数字相对应的 NMR 波谱:S11、S19、S22、S26、S28、S30、S33、S36、S56、S59、S61、S70、S72、S74、S76 和 S78。

3) In some spectra, compound structures appear multiple times. Kindly review and remove any duplicate structures.
3) 在某些光谱中,化合物结构出现多次。请检查并删除任何重复的结构。

4) Also, check for any instances where compound structures are overlapping with NMR peaks and adjust accordingly.
4) 此外,检查化合物结构与 NMR 峰重叠的任何情况,并进行相应调整。

Reviewer: 2
审稿人:2

Recommendation: Publish in The Journal of Organic Chemistry without change.
建议:在 The Journal of Organic Chemistry 上发表,不做任何更改。

Comments:

Excellent job¡¡¡

I is not easy working with these chiral imines undef photochemical conditions.
我不容易使用这些手性亚胺 undef 光化学条件。

Reviewer: 3
审稿人: 3

Recommendation: The manuscript may be publishable, but it should be reviewed after major revisions.
建议:手稿可以发表,但应在进行重大修改后进行审查。

Comments:

Xiao, Liao and coworkers reported a photocatalytic [3+2] cycloaddition of nonstabilized azomethine ylides with chiral sulfonamides, enabling the synthesis of chiral imidazolidines under mild conditions. Additionally, the products could be converted into chiral 1,2-diamines. The manuscript documents a promising alternative to access such valuable compounds and is well-organized. However, the exploration of photocatalysts, the applicability of the method, and the evidence for the proposed mechanism are insufficient. Therefore, I believe that the manuscript must be revised as follows before it can be published.
Xiao、Liao 及其同事报道了非稳定的偶氮甲嘧啶酰化物与手性磺胺类药物的光催化 [3+2] 环加成反应,能够在温和条件下合成手性咪唑烷。此外,该产物可以转化为手性 1,2-二胺。该手稿记录了一种有前途的替代方案来获得如此有价值的化合物,并且组织良好。然而,对光催化剂的探索、该方法的适用性以及所提出的机制的证据不足。因此,我认为在发表之前,必须将稿件修改如下。

1. The applications of azomethine ylide precursor 2 in photochemical reactions and the related literatures should be discussed [e.g. the seminal work (Ref. 8d) and the recent work (Adv. Synth. Catal. 2023, 365, 4303)].
1. 应讨论偶氮甲嘧啶酰化物前驱体 2 在光化学反应中的应用和相关文献 [例如,开创性工作(参考文献 8d)和最近的工作(Adv. Synth.加泰罗尼亚。2023, 365, 4303)].

2. In addition to metal-based photocatalysts, it is also recommended to investigate the catalytic efficiency of typical organic photocatalysts such as Eosin Y and Rose Bengal (Table 1).
2. 除了金属基光催化剂外,还建议研究典型的有机光催化剂,如 Eosin Y 和 Rose Bengal(表 1)。

3. Only three para-substituted benzyl dipole precursors were evaluated (Table 3). The applicability of the method to meta- or ortho-substituted benzyl precursors and other alkyl precursors should be investigated.
3. 仅评估了三种对位取代的苄基偶极子前驱体(表 3)。应研究该方法对间位或邻位取代的苄基前驱体和其他烷基前驱体的适用性。

4. It is not enough to support the reaction mechanism only through radical trapping experiments (Table 4). UV-visible absorption spectra and Stern-Volmer fluorescence quenching are recommended to investigate to further support the proposed mechanism.
4. 仅通过自由基捕获实验来支持反应机制是不够的(表 4)。建议研究紫外-可见吸收光谱和 Stern-Volmer 荧光猝灭,以进一步支持所提出的机制。

5. Are there any recent papers corresponding to the topics of References 2 and 3?
5. 是否有与参考文献 2 和 3 主题相对应的近期论文?

6. The H NMR spectra of compounds 3a, 4, 7, 17, 18, 19, and 39 show significant peaks of water or impurities, which require further purification. In addition, the integral values in the H NMR spectra of almost all products are integers, which might be intentional.
6. 化合物 3a、4、7、17、18、19 和 39 的 H NMR 波谱显示明显的水或杂质峰,需要进一步纯化。此外,几乎所有产品的 H NMR 波谱中的积分值都是整数,这可能是有意为之。