1360567-60-7Relevant articles and documents
Photoinduced C-H direct arylation of unactivated arenes
Kan, Jian,Huang, Shijun,Zhao, Huaiqing,Lin, Jin,Su, Weiping
, p. 1329 - 1333 (2015)
Two general protocols have been developed for the photoinduced, metal-free direct arylation of unactivated arenes with aryl iodide. Both methods gave good to excellent yields for most substrates. Notably, the C-F bond in method A and the C-F, C-Cl, and C-Br bonds in method B could survive the arylation reaction. These methods offered excellent options for syntheses of biaryls.
Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides
Malapit, Christian A.,Bour, James R.,Brigham, Conor E.,Sanford, Melanie S.
, p. 100 - 104 (2018)
The Suzuki–Miyaura cross-coupling of organoboron nucleophiles with aryl halide electrophiles is one of the most widely used carbon–carbon bond-forming reactions in organic and medicinal chemistry1,2. A key challenge associated with these transformations is that they generally require the addition of an exogenous base, the role of which is to enable transmetallation between the organoboron nucleophile and the metal catalyst3. This requirement limits the substrate scope of the reaction because the added base promotes competitive decomposition of many organoboron substrates3–5. As such, considerable research has focused on strategies for mitigating base-mediated side reactions6–12. Previous efforts have primarily focused either on designing strategically masked organoboron reagents (to slow base-mediated decomposition)6–8 or on developing highly active palladium precatalysts (to accelerate cross-coupling relative to base-mediated decomposition pathways)10–12. An attractive alternative approach involves identifying combinations of catalyst and electrophile that enable Suzuki–Miyaura-type reactions to proceed without an exogenous base12–14. Here we use this approach to develop a nickel-catalysed coupling of aryl boronic acids with acid fluorides15–17, which are formed in situ from readily available carboxylic acids18–22. This combination of catalyst and electrophile enables a mechanistic manifold in which a ‘transmetallation-active’ aryl nickel fluoride intermediate is generated directly in the catalytic cycle13,16. As such, this transformation does not require an exogenous base and is applicable to a wide range of base-sensitive boronic acids and biologically active carboxylic acids.
Synthesis and catalytic activity of ionic palladium N-heterocyclic carbene complexes
Ya?ar, Sedat,Akko?, Mitat,?zdemir, Nam?k,?zdemir, ?smail
, p. 1622 - 1633 (2019)
The synthesis of 3 benzimidazole-based ionic Pd(II)-NHC complexes (NHC: N -heterocyclic carbene) is presented. The structures of the complexes are as follows: [NHC-PdBr 3 ] ? [NHC] + . The ionic palladium(II)-NHC complexes were synthesized in high yields and were fully characterized by nuclear magnetic resonance spectroscopy, X-ray diffraction, LC-MS/MS, and elemental analysis. These complexes have been identified as active catalysts in Suzuki–Miyaura reactions in a solution of 2-propanol and water at room temperature for different aryl bromides.
A novel ditopic ring-expanded N-heterocyclic carbene ligand-assisted Suzuki-Miyaura coupling reaction in aqueous media
Karaca, Emine ?zge,Akko?, Mitat,Nawaz Tahir, Muhammad,Ar?c?, Cengiz,?mik, Fatma,Gürbüz, Nevin,Ya?ar, Sedat,?zdemir, ?smail
supporting information, p. 3529 - 3532 (2017/10/06)
A series of seven-membered ditopic ring-expanded N-heterocyclic carbene (dre-NHC) precursors, bearing sterically demanding and electron-rich aryl groups, were synthesised in moderate yields via the reaction of 1,2,4,5-tetrakis(bromomethyl)benzene with the corresponding N,N′-diarylformamidines in the presence of K2CO3 in acetonitrile under an air atmosphere. All new compounds were characterised by HRMS, NMR spectroscopy, and microanalysis, as well as X-ray crystallography for compound 1c. The development of an efficient catalytic system for the Suzuki-Miyaura coupling reaction of aryl chlorides with various boronic acids was also investigated using the in situ generated dre-NHC ligands.
Modular Approach to Heterogenous Catalysis. Manipulation of Cross-Coupling Catalyst Activity
Stibingerova, Iva,Voltrova, Svatava,Kocova, Sarka,Lindale, Matthew,Srogl, Jiri
supporting information, p. 312 - 315 (2016/02/03)
A new type of robust, heterogeneous, modular Pd catalyst with metal embedded in the gel matrix is presented. The regulatory element of its catalytic activity has been introduced via chemical changes in the gel. The concept is illustrated in a series of Suzuki-Miyaura cross-coupling reactions. The demonstrated catalyst activity variations depend on the structure of the gel.
