Rapid Assessment of the Reaction‐Condition‐Based Sensitivity of Chemical Transformations

Abstract

As ystematic,u ser-friendly assessment tool that delivers ac lear overview of the sensitivity of reactions to key parameters is highly desirable.Herein, the development of such amethod is described. The intuitive,standardized presentation of the results in ar adar diagram enables the sensitivity of ap rotocol to be rapidly assessed. This method was applied to five different visible-light-mediated photochemical reactions, and the results were correlated to the underlying mechanism. Ultimately,webelieve that this assessment will help to increase the uptake of new synthetic methods and their reproducibility. Angewandte Chemie Communications

Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect

“…Control experiments with respect to the photosensitizer as well as light irradiation further demonstrated the necessity of each component. Additionally, to further identify the crucial parameters for our reaction, a systematic reaction‐parameter‐based sensitivity screen was performed (Table , radar diagram) . Notably, the reaction was found to be sensitive towards low light intensity and high oxygen concentration, but robust in terms of the moisture sensitivity and temperature fluctuations (Section S3.2).…”

“…crucial parameters for our reaction, as ystematic reactionparameter-based sensitivity screen was performed ( Table 1, radar diagram). [29] Notably,t he reaction was found to be sensitive towards low light intensity and high oxygen concen-tration, but robust in terms of the moisture sensitivity and temperature fluctuations (Section S3.2).…”

Carbene‐Catalyzed Enantioselective Aromatic N‐Nucleophilic Addition of Heteroarenes to Ketones

“…To our delight, the enantioselectivity could be further improved when carrying out the reaction with 5 mol % of NHC catalyst E at 10 °C, where the excellent yield of 3 a was retained (entry 12). On a technical note, the N , O ‐acetal product 3 a exhibited good stability under these conditions and the reaction also showed tolerance to slight condition variations …”

Gadolinium Photocatalysis: Dearomative [2+2] Cycloaddition/Ring‐Expansion Sequence with Indoles

“…[22] Therefore,w ee xamined how the reaction outcome could be affected by key reaction param-eters and the results are displayed in Table 1. [23] Accordingly,w hen performing the reaction at high temperature or high oxygen atmosphere,t his transformation becomes sluggish. In contrast, lower temperature,m edium oxygen concentration, as well as the distance to the light source,the concentration of the substrates,a nd the reaction scale show only aslight influence on the outcome.…”