95753-22-3Relevant articles and documents
Ipso- borylation of aryl ethers via Ni-Catalyzed C-OMe Cleavage
Zarate, Cayetana,Manzano, Rubén,Martin, Ruben
supporting information, p. 6754 - 6757 (2015/06/16)
A Ni-catalyzed ipso-borylation of aryl ethers via C(sp2)-OMe and C(sp3)-OMe cleavage is described. The transformation is characterized by its wide substrate scope under mild conditions and an exquisite divergence in site selectivity that can be easily switched by selecting the appropriate boron reagent.
Beyond directed ortho metalation: Ru-catalyzed CAr-O activation/cross-coupling reaction by amide chelation
Zhao, Yigang,Snieckus, Victor
supporting information, p. 11224 - 11227 (2014/09/29)
Disclosed is a new, catalytic, and general methodology for the chemical synthesis of biaryl, heterobiaryl, and polyaryl molecules by the cross-coupling of o-methoxybenzamides with aryl boroneopentylates. The reaction is based on the activation of the unreactive C-OMe bond by the proximate amide directing group using catalytic RuH2(CO)(PPh3)3 conditions. A one-step, base-free coupling process is thereby established that has the potential to supersede the useful two-step directed ortho metalation/cross- coupling reaction involving cryogenic temperature and strong base conditions. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, minimum waste, and convenient scale-up make these reactions suitable for industrial applications.
Neopentylglycolborylation of ortho -substituted aryl halides catalyzed by NiCl2-Based mixed-ligand systems
Moldoveanu, Costel,Wilson, Daniela A.,Wilson, Christopher J.,Leowanawat, Pawaret,Resmerita, Ana-Maria,Liu, Chi,Rosen, Brad M.,Percec, Virgil
supporting information; experimental part, p. 5438 - 5452 (2010/11/05)
NiCl2-based mixed-ligand systems were shown to be very effective catalysts for the neopentylglycolborylation of aryl iodides, bromides, and chlorides bearing electron-rich and electron-deficient ortho-substituents. Although NiCl2-based single-ligand catalytic systems were able to mediate neopentylglycolborylation of selected substrates, they were not as effective for all substrates, highlighting the value of the mixed-ligand concept. Optimization of the Ni(II)-catalyzed neopentylglycolborylation of 2-iodoanisole and methyl 2-iodobenzoate demonstrated that, while the role of ligand and coligand in the conversion of Ni(II) precatalyst to Ni(0) active catalyst cannot be ignored, a mixed-ligand complex is likely present throughout the catalytic cycle. In addition, protodeborylation and hydrodehalogenation were demonstrated to be the predominant side reactions of Ni(II)-catalyzed borylation of ortho-substituted aryl halides containing the electron-deficient carboxylate substituents. Ni(II) complexes in the presence of H2O and Ni(0) are responsible for the catalysis of these side reactions.
