90433-31-1Relevant academic research and scientific papers
Cyclopropyl boronic derivatives in parallel synthesis of sp 3-enriched compound libraries
Grygorenko, Oleksandr O.,Kleban, Ihor,Konovets, Angelika I.,Radchenko, Dmytro S.,Rassukana, Yuliya,Shuvakin, Serhii,Tymtsunik, Andriy V.
, (2020)
Abstract: The Suzuki–Miyaura coupling of cyclopropyl boronic derivatives with (het)aryl halides was evaluated as a method for parallel synthesis of sp3-enriched compound libraries. The scope and limitation of the procedure were established. It was shown that the method was applicable to a wide range of cyclopropyl trifluoroborates and (het)aryl bromides. Limitations of the method included trifluoroborates bearing bulky substituents at the α position, as well as (het)aryl bromides with ester moieties. A 96-member library was prepared to illustrate the concept with 68% success rate and 30% average yield. Calculated physico-chemical properties of the products obtained (in particular, sp3-hybrid carbon atom fraction Fsp3 = 0.16-0.83 range, 0.52 on average), as well as neglectable “LogP drift” effect, observed experimentally (0.02 units) showed that the method is well-compatible with lead-oriented synthesis criteria. Graphic abstract: [Figure not available: see fulltext.]
1,3-Oxyalkynylation of Aryl Cyclopropanes with Ethylnylbenziodoxolones Using Photoredox Catalysis
Studer, Armido,Zuo, Zhijun
supporting information, p. 949 - 954 (2022/02/07)
Alkynes and cyclopropanes are vital motifs in chemistry. Herein, a photoredox catalyzed 1,3-oxyalkynylation of aryl cyclopropanes with ethylnylbenziodoxolones (EBXs) in an atom-economic fashion is described. This cascade comprises single-electron oxidatio
Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes
Daniliuc, Constantin G.,Studer, Armido,Zuo, Zhijun
supporting information, p. 25252 - 25257 (2021/10/29)
Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.
Redox-photosensitized aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia
Yasuda, Masahide,Kojima, Ryuji,Tsutsui, Hiroshi,Utsunomiya, Daigo,Ishii, Kazuaki,Jinnouchi, Koutaro,Shiragami, Tsutomu
, p. 7618 - 7624 (2007/10/03)
1,2,4-Triphenylbenzene and 2,2′-methylenedioxy-1,1′ -binaphthalene successfully photosensitized the aminations of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia and primary amines in the presence of m- or p-dicyanobenzene, which gave the 4-amino-1,2-benzocycloalkenes, 3-amino-1-arylpropanes, and 7-amino-5-(p-cyanophenyl)bicyclo[2.2.1]hept-2-ene, respectively. A key pathway for the photosensitized amination is the hole transfer from the cation radicals of the sensitizers that were generated by photoinduced electron transfer to the electron acceptors to the substrates. Therefore, it was found that the relationships in oxidation potentials between the sensitizers and the substrates and the positive charge distribution of the cation radicals of the substrates were important factors for the efficient amination.
Reactivity of Aryl Vinyl Di-?-methane Systems. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Swafford, Richard L.
, p. 3069 - 3083 (2007/10/02)
The di-?-methane rearrangement of a series of meta and para substituted arylvinylmethane reactants was investigated with the aim of determiningthe patterns of reactivity in systems in which initial excitation is localized in the aryl moiety.Thus the photo
