Reposted by Mathias Senge
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Mathias Senge
@mathiassenge.bsky.social
590 followers 129 following 46 posts
Chair of Organic Chemistry - TCD, Alumnus Hans Fischer Senior Fellow - TU Munich. Organic synthesis, light, structures, porphyrins in all shapes and historical settings
![Bicyclo[1.1.1]pentane is a rigid aliphatic hydrocarbon with a three-dimensional (3D), propeller-like shape and a molecular size which makes it a targeted bioisosteric replacement for phenylene and acetylene groups in medicinal chemistry. For the pharmaceutical application of BCP, simple, efficient, and cost-effective synthetic tools are required to enable the exploration of BCP’s potential as a bioisostere across a broad chemical space. The synthesis of BCP mono- and diketones remains a challenging task, limited by both substrate scope and expensive photocatalysts. Here we present a protocol for Friedel-Crafts acylation of (hetero)aromatic hydrocarbons with BCP acyl chlorides; in particular, the first method to access diaromatic BCP 1,3-diketones. Reaction optimization, substrate scope, and reactivity of the products are discussed. 35 mono- and diketones are reported accompanied by 7 examples of post-synthetic modifications. The synthesis of a BCP analogue of fenofibrate is reported.](https://cdn.bsky.app/img/feed_thumbnail/plain/did:plc:ls54voiihm3bxde2dkgrxbm3/bafkreigzyfnz4ckoa7ifg3rjuuzk7tt3vdih5xlizy6ledhqn5ua3urgie)
![Bimanes, a class of molecules based on the 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione scaffold, were first introduced by E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a promising strategy for synthesizing substituted cyclobutanes without the need for ultraviolet irradiation.](https://cdn.bsky.app/img/feed_thumbnail/plain/did:plc:ls54voiihm3bxde2dkgrxbm3/bafkreidduymtzhb44xcfbfd46fwrtmmzmgmj7u6dbks42otca4k5xfa37i)
