577-92-4Relevant articles and documents
Iron-Catalyzed Room Temperature Cross-Couplings of Bromophenols with Aryl Grignard Reagents
Xu, Li-Chen,Liu, Kun-Ming,Duan, Xin-Fang
supporting information, p. 5421 - 5427 (2019/11/14)
Herein we report a room temperature Fe-catalyzed coupling reaction of various bromophenols with aryl Grignard reagents, which exhibits a wide substrate scope and high functional group tolerance. For the first time, the combination of simple Fe(acac)3/PBu3/Ti(OEt)4 has been used as an effective catalyst for the biaryl couplings of bromophenols or their Na or K salts with debromination and etherification side reactions being well suppressed. Various biphenols including natural product garcibiphenyl C as well as pharmaceutical diflunisal and its ethyl ester were facilely synthesized using the present protocol. (Figure presented.).
Adiabatic deprotonation as an important competing pathway to ESIPT in photoacidic 2-phenylphenols
Mena, Leandro D.,Vera,Baumgartner, Maria T.,Jimenez, Liliana B.
, p. 12231 - 12240 (2019/06/20)
ESIPT (Excited State Intramolecular Proton Transfer) to C atom in 2-phenylphenol is known to be an intrinsically inefficient process. However, to the best of our knowledge, a structure-ESIPT efficiency relationship has not been elucidated yet. Here, we show that there exists a competitive interplay between photoacidity and ESIPT efficiency for the 2-phenylphenol system. The attachment of electron withdrawing groups to the phenol moiety promotes adiabatic deprotonation in the excited state and diminishes the charge transfer character of the excitations, and both these factors contribute in decreasing the ESIPT reaction yield. On the other hand, unfavorable conformational distribution in the ground state also appears as another important aspect responsible for the low ESIPT extent of 2-phenylphenol. A new derivative bearing electron donating, bulky substituents at ortho and para positions of the phenol ring shows an outstanding ESIPT performance, which demonstrates that the efficiency of the process can be significantly enhanced by modifying the substitution pattern. We anticipate that our results will help to guide the molecular designing of new compounds with high ESIPT efficiency.
Copper-catalyzed selective ortho-arylations of 2-naphthol and phenol derivatives with diaryliodonium salts
Qian, Xiaofei,Han, Jianwei,Wang, Limin
, p. 607 - 610 (2016/01/20)
The selective arylations of 2-naphthol and phenol derivatives catalyzed by Cu(OTf)2 with using diaryliodonium(III) salts have been developed. With this method, biaryls bearing hydroxyl groups can be easily accessed in moderate to good yields. Additionally, this protocol provided an alternative for the preparation of 3-arylated binaphthalene derivatives.