Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions.

Autor: Yi L; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Kong D; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Prabhakar Kale A; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Alshehri R; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Yue H; Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University), College of Chemistry, Fuzhou University, 350108, Fuzhou, China., Gizatullin A; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Maity B; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Kancherla R; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Cavallo L; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia., Rueping M; KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), 23955-6900, Thuwal, Saudi Arabia.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 16; Vol. 63 (51), pp. e202411961. Date of Electronic Publication: 2024 Oct 30.
DOI: 10.1002/anie.202411961
Abstrakt: Bicyclo[1.1.1]pentane (BCP), recognized as a bioisostere for para-disubstituted benzene, has gained widespread interest in drug development due to its ability to enhance the physicochemical properties of pharmaceuticals. In this work, we introduce a photoinduced, halogen bonding-initiated, metal-free strategy for synthesizing various BCP derivatives. This method involves the generation of nucleophilic α-aminoalkyl radicals via halogen-bonding adducts. These undergo selective radical addition to [1.1.1]propellane, yielding electrophilic BCP radicals that subsequently participate in polarity-matched additions, culminating in the difunctionalization of bicyclopentane. The versatility and practicality of this metal-free approach are underscored by its broad substrate scope, which includes late-stage functionalization and a series of valuable transformations, all conducted under mild reaction conditions.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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