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Article summary:
1. Substituted benzene rings are a common component of many drugs and agrochemicals, but they can suffer from metabolic modifications that lead to toxic metabolites.
2. To improve biological activity, pharmacological potency, and physicochemical properties, the replacement of substituted benzenes with saturated polycyclic C(sp3)-rich hydrocarbon scaffolds is now a standard approach in medicinal chemistry and crop science.
3. This article presents a catalytic alkene insertion approach to bicyclo[2.1.1]hexane bioisosteres as an efficient method for synthesizing 1,2- and 1,4-disubstituted BCHs for evaluation in medicinal and agrochemical settings.
Article analysis:
The article “A catalytic alkene insertion approach to bicyclo[2.1.1]hexane bioisosteres” by Nature Chemistry is generally reliable and trustworthy due to its clear presentation of evidence supporting its claims and its balanced discussion of both the potential benefits and risks associated with the proposed method for synthesizing BCHs. The article provides a comprehensive overview of the current state of research on substituted benzene rings in pharmaceuticals and agrochemicals, as well as the need for improved metabolic stability in drug analogues, which has led to the development of saturated hydrocarbon bioisosteres such as BCPs, bicyclo[2.2.2]octanes, cubanes, and BCHs as alternatives to substituted benzenes. It then goes on to describe how this article presents a catalytic alkene insertion approach using SmI2 as a catalyst that can be used to access these BCH bioisosteres with complete regiocontrol and high atom economy.
The article is also unbiased in its presentation of evidence; it provides detailed descriptions of experiments conducted to optimize reaction conditions for the catalytic alkene insertion process as well as surveys of BCB ketones 11 that can participate in the reaction and alkenes 12 that can be coupled with representative BCB ketone 11a. Furthermore, it includes computational studies suggesting that the catalytic alkene insertion occurs via a radical relay mechanism triggered by reversible single electron transfer from SmI2 to ketones 11, which further supports its claims regarding the efficacy of this method for synthesizing BCHs.
In conclusion, this article is reliable and trustworthy due to its clear presentation