biostudies-literatureUnknown20van der Heide PThe rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkylation. In this research, we present a metal-free strategy for the photochemical alkylation of dehydroalanine derivatives. Upon abstraction of a hydride from tris(trimethylsilyl)silane (TTMS) by an exciBeilstein journal of organic chemistry3274-3280https://www.ebi.ac.uk/biostudies/studies/S-EPMC11665442biostudies-literatureGiese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.PMC11665442Luridiana APiersanti GRetini MFanini FNoel Tvan der Heide PMazzarella DSecci FfalseGiese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.The rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkylation. In this research, we present a metal-free strategy for the photochemical alkylation of dehydroalanine derivatives. Upon abstraction of a hydride from tris(trimethylsilyl)silane (TTMS) by an exci2024-01-01T00:00:00Z20242025-04-18T12:46:04.579Z2025-04-06T22:11:49.639ZS-EPMC116654423971726410.3762/bjoc.20.271