66464-20-8Relevant academic research and scientific papers
Rhodium-catalyzed Si-F exchange reaction between fluorobenzenes and a disilane. Catalytic reaction involving cleavage of C-F bonds
Ishii, Yutaka,Chatani, Naoto,Yorimitsu, Shuhei,Murai, Shinji
, p. 157 - 158 (1998)
The reaction of functionalized fluorobenzenes, such as fluoroacetophenones and (fluorophenyl)oxazolines, with Me3SiSiMe3 in the presence of a catalytic amount of a rhodium complex results in a site-selective Si-F exchange to give ort
NHC-Copper Mediated Ligand-Directed Radiofluorination of Aryl Halides
Sharninghausen, Liam S.,Brooks, Allen F.,Winton, Wade P.,Makaravage, Katarina J.,Scott, Peter J. H.,Sanford, Melanie S.
supporting information, p. 7362 - 7367 (2020/08/19)
[18F]-labeled aryl fluorides are widely used as radiotracers for positron emission tomography (PET) imaging. Aryl halides (ArX) are particularly attractive precursors to these radiotracers, as they are readily available, inexpensive, and stable. However, to date, the direct preparation of [18F]-aryl fluorides from aryl halides remains limited to SNAr reactions between highly activated ArX substrates and K18F. This report describes an aryl halide radiofluorination reaction in which the C(sp2)-18F bond is formed via a copper-mediated pathway. Copper N-heterocyclic carbene complexes serve as mediators for this transformation, using aryl halide substrates with directing groups at the ortho position. This reaction is applied to the radiofluorination of electronically diverse aryl halide derivatives, including the bioactive molecules vismodegib and PH089.
Aerobic C(sp2)-H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
G?bel, Dominik,Clamor, Nils,Lork, Enno,Nachtsheim, Boris J.
supporting information, p. 5373 - 5377 (2019/06/07)
The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl·LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
Synthesis of nickel and palladium complexes with diarylamido-based unsymmetrical pincer ligands and application for norbornene polymerization
Liu, Hui,Yuan, Haibin,Shi, Xiaochao
, p. 609 - 617 (2019/01/08)
A set of diarylamido-based unsymmetrical [PNNox] pincer ligands containing a chiral oxazoline ring have been synthesized and their nickel and palladium complexes [(2-PPh2(R1)ArN(R1)Ar-2-(R)oxazoline)MCl] (R1 = 4-H, R = (S)-4-iPr, M = Pd (Pd1); R1 = 4-H, R = (S)-4-Bn, M = Pd (Pd2); R1 = 4-H, R = (S)-4-Ph, M = Pd (Pd3); R1 = 4-Me, R = (S)-4-Bn, M = Pd (Pd4); R1 = 4-Me, R = (S)-4-Ph, M = Pd (Pd5); R1 = 4-H, R = 4-Me2, M = Pd (Pd6); R1 = 4-H, R = Benzo[d]-, M = Pd (Pd7); R1 = 4-H, R = (S)-4-Bn, M = Ni (Ni1); R1 = 4-H, R = (S)-4-Ph, M = Ni (Ni2); R1 = 4-Me, R = (S)-4-Bn, M = Ni (Ni3); R1 = 4-Me, R = (S)-4-Ph, M = Pd (Ni4)) were tested to show high catalytic activities for polymerization of norbornene. After activation of methylaluminoxane (MAO), all the nickel and palladium complexes could catalyze the polymerization of norbornene to yield vinyl-type polymers with activities up to 40.3 × 105 g of PNB (mol of Pd)?1 h?1. The copolymerization of norbornene with functional norbornene comonomers was also investigated by catalyst Pd2, accompanied by decreased catalytic activity and low incorporation of functional comonomers.
Palladium-catalyzed electrophilic C–H fluorination of arenes using oxazoline as a removable directing group
Gutierrez, David A.,Lee, Wan-Chen Cindy,Shen, Yuning,Li, Jie Jack
, p. 5372 - 5376 (2016/11/11)
Dimethyloxazoline was rationally designed to act as a removable ortho-directing group (DG) for the palladium-catalyzed C–H electrophilic fluorination of arenes. Using NFSI as the fluorinating agent, and Pd(II), Ag(I) catalytic system, electrophilic C(sp2–H) ortho-fluorination took place on a variety of aryl substrates to afford the corresponding mono- and di-fluorinated products.
Directed functionalization of halophenyl-2-oxazolines with TMPMgCl?LiCl
Batista, Joo H. C.,Santos, Fernanda M. Dos,Bozzini, Leandro A.,Vessecchi, Ricardo,Oliveira, Alfredo R. M.,Clososki, Giuliano C.
, p. 967 - 977 (2015/02/19)
A variety of difunctionalized aryl-2-oxazolines were prepared from the reaction of halophenyl-2-oxazolines and TMPMgCl?LiCl to give an organomagnesium reagent, which was then treated with various electrophiles. The metalation step takes place under mild conditions, and this process al-lows for the isolation of the desired products in good yields. No isomeric or other benzyne-derived products were detected. The influence of the halogen substituents on the acidity of the aromatic hydrogen atoms was evaluated by using density functional theory (DFT) calculations.
Ortho-directed functionalization of arenes using magnesate bases
Bellamy, Estelle,Bayh, Omar,Hoarau, Christophe,Trecourt, Francois,Queguiner, Guy,Marsais, Francis
supporting information; experimental part, p. 7043 - 7045 (2010/11/02)
Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.
Synthesis and structural characterization of new phosphinooxazoline complexes of iron
Sedinkin, Sergey L.,Rath, Nigam P.,Bauer, Eike B.
, p. 3081 - 3091 (2008/12/22)
The first phosphinooxazoline chelate complexes of iron were synthesized, and their structural and electronic properties were studied. The known phosphinooxazolines 2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole (7a), 2-(2-(diphenylphosphino)phenyl)-4,
Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines
Peer, Markus,De Jong, Johannes C.,Kiefer, Matthias,Langer, Thomas,Rieck, Heiko,Schell, Heico,Sennhenn, Peter,Sprinz, Juergen,Steinhagen, Henning,Wiese, Burkhard,Helmchen, Guenter
, p. 7547 - 7583 (2007/10/03)
A series of enantiomerically pure 2-[2-(diarylphosphino)aryl]-oxazolines was prepared from commercially available or synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid (ii) ZnCl2 catalyzed condensation with a 2-halobenzonitrile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorous were prepared by either diastereoselective nucleophilic substitution of halogenide of Ar1Ar2PCl or by nucleophilic aromatic substitution with LiPAr1Ar2. In addition, sulfur and selenium analogs were prepared.
