Content of review 1, reviewed on November 26, 2023

In this manuscript, Dell'Amico and coworkers present a photoredox protocol for the (3+2) cycloaddition of aziridines to afford a series of pyrrolidines and dihydropyrroles with high chemo-, regio- and diastereoselectivity. This protocol presumably proceeds via forming reactive azomethine ylides through photoinduced two consecutive SET events. A broad range of substrate scope with aziridines, dipolarophiles, and alkynes is compatible with high yields under mild conditions. The authors also demonstrated this method's synthetic utility by synthesizing fluorescent probes. Mechanistic investigations are also nicely presented. Overall, this referee supports its publication in Chemical Science.
The following issues are to be addressed:
1, Fig 2, the dr ratios of products 29-34 decreased significantly. What is the reason? Related comments should be included. Also, on Page 3, the comment, "In all the cases, the reactions furnished the desired cycloaddition products with high diastereoselectivity (up to >20:1 dr) and 40-79% yield.", "high diastereoselectivity (up to >20:1 dr)" conflicts with the results of these products (29- 34). Please check and revise accordingly.

  1. Have these fluorescent probes shown in Fig. 5 measured the fluorescence lifetime?
  2. A related Photoinduced [3+2} cycloaddition of N-tosyl aziridines and alkenes work is miss cited with comments(Chu, Org. Chem. Front. 2021, 8, 2196-2202.).
    4, In SI, the general procedure D "this reaction was irradiated with a Kessil 427 nm lamp set at 50%,". What is the real light intense? And how about the reaction efficiency if the lamp is set at 25%, 75%, or 100%?
    5, In SI, several NMR spectra show significant impurities, such as 19, 23, and 29. please address them.
    6, In SI, the structure of S60 sees wrong. Please check it and correct it if necessary.

Source

    © 2023 the Reviewer.

References

    Daniele, M., Tommaso, B., Giorgio, P., Luca, D. 2023. Photocatalytic (3+2) dipolar cycloadditions of aziridines driven by visible-light. Chemical Science.