Modular allylation of C(sp3)–H bonds by combining decatungstate photocatalysis and HWE olefination in flow?
Chemical Science Pub Date: 2022-05-31 DOI: 10.1039/D2SC01581A
Abstract
The late-stage introduction of allyl groups provides an opportunity to synthetic organic chemists for subsequent diversification, furnishing a rapid access to new chemical space. Here, we report the development of a modular synthetic sequence for the allylation of strong aliphatic C(sp3)–H bonds. Our sequence features the merger of two distinct steps to accomplish this goal, including a photocatalytic Hydrogen Atom Transfer and an ensuing Horner–Wadsworth–Emmons (HWE) reaction. This practical protocol enables the modular and scalable allylation of valuable building blocks and has been applied to structurally complex molecules.
Recommended Literature
- [1] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [2] An automatic determination of thoria in thoria-urania mixtures Analyst, 1966,91, 208-210 10.1039/AN9669100208
- [3] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [4] An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines? Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. PatureauChem. Commun., 2019,55, 13749-13752 10.1039/C9CC05240B
- [5] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
- [6] An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions? Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng CaoJ. Mater. Chem. A, 2014,2, 7662-7665 10.1039/C4TA00313F
- [7] An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform? Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao YouAnalyst, 2015,140, 1827-1831 10.1039/C4AN01953A
- [8] An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs) R. M. Pemberton,J. P. Hart,T. T. MottramAnalyst, 2001,126, 1866-1871 10.1039/B104874K
- [9] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
- [10] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
Journal Name:Chemical Science
research_products
-
CAS no.: 89640-58-4