87150-14-9Relevant articles and documents
Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts
Shi, Xinzhe,Soulé, Jean-Fran?ois,Doucet, Henri
, p. 4748 - 4760 (2019/09/12)
Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).
Nickel-catalyzed decarboxylative arylation of heteroarenes through sp2 C-H functionalization
Yang, Ke,Wang, Peng,Zhang, Cheng,Kadi, Adnan A.,Fun, Hoong-Kun,Zhang, Yan,Lu, Hongjian
supporting information, p. 7586 - 7589 (2015/04/22)
The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C-H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aroma
Copper-mediated dehydrogenative biaryl coupling of naphthylamines and 1,3-azoles
Odani, Riko,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
, p. 11045 - 11052 (2013/11/19)
A copper-mediated dehydrogenative biaryl cross-coupling of naphthylamines and 1,3-azoles has been developed. The key to its success is the introduction of N,N-bidentate coordination system based on the picolinamide directing group. The reaction proceeds s