71885-44-4Relevant academic research and scientific papers
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.
Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands
Ghorai, Debasish,Müller, Valentin,Keil, Helena,Stalke, Dietmar,Zanoni, Giuseppe,Tkachenko, Boryslav A.,Schreiner, Peter R.,Ackermann, Lutz
supporting information, p. 3137 - 3141 (2017/09/06)
C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides
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.
C-H bond arylations and benzylations on oxazol(in)es with a palladium catalyst of a secondary phosphine oxide
Ackermann, Lutz,Barfuesser, Sebastian,Kornhaass, Christoph,Kapdi, Anant R.
supporting information; experimental part, p. 3082 - 3085 (2011/08/07)
An air-stable, well-defined palladium complex derived from secondary phosphine oxide (SPO) (1-Ad)2P(O)H enabled efficient C-H bond functionalizations with ample scope, which set the stage for direct arylations and benzylations of (benz)oxazoles, as well as unprecedented palladium-catalyzed C-H bond arylations on nonaromatic oxazolines.
Chiral lithium amide mediated asymmetric synthesis of 3-aryl-3,4- dihydroisocoumarins
Sharma, Arvind Kumar,Maheshwary, Yogita,Singh, Paramjit,Singh, Kamal Nain
experimental part, p. 54 - 62 (2010/10/19)
An asymmetric synthesis of 3-aryl-3,4-dihydroisocoumarins using the reaction of laterally lithiated 4,4-dimethyl-2-(o-tolyl)oxazoline with aromatic aldehydes, in the presence of an external chiral ligand, gave products with enantiomeric excess (ee) in the range of 60-70%. ARKAT USA, Inc.
Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter
Chen, Xiao,Li, Jiao-Jie,Hao, Xue-Shi,Goodhue, Charles E.,Yu, Jin-Quan
, p. 78 - 79 (2007/10/03)
The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C-H bonds with organometallic reagents. A variety of tetraalkyltins were coupled to C-H bonds to give the alkylated products in good yields by using 5 mol % Pd(OAc)2 as the catalyst. Benzoquinone was shown to be essential for the C-H activation when substrates containing non-π-conjugated chelating groups are used. Monitoring the formation and reductive elimination of the Pd(Ar)(Me)L2 complex also revealed that benzoquinone promotes the reductive elimination step. Microwave irradiation enhances the reaction rate drastically. The versatility of this protocol was demonstrated by using substrates containing either oxazoline or pyridine as directing groups. Copyright
A facile one stage synthesis of oxazolines under microwave irradiation
Clarke, David S.,Wood, Robin
, p. 1335 - 1340 (2007/10/03)
A rapid, high yielding procedure for the synthesis of 2-substituted oxazolines has been achieved under microwave irradiation from alkyl and aryl nitriles and β-amino alcohols using a mild Lewis acid catalyst.
