62892-76-6Relevant academic research and scientific papers
Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Involving C?O Bond Activation
Morishige, Aoi,Iyori, Yasuaki,Chatani, Naoto
, (2021/07/17)
An efficient Suzuki-Miyaura cross-coupling reaction of ortho-phenoxy-substituted aromatic amides with aryl boronates is described. The use of LiOtBu is crucial for the success of the reaction. An amidate anion, which is formed through deprotonation of the amide NH bond by LiOtBu, functions as a directing group to activate a C?O bond.
Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
supporting information, p. 15267 - 15271 (2019/12/11)
Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
Intramolecular metal-free oxidative aryl-aryl coupling: An unusual hypervalent-iodine-mediated rearrangement of 2-substituted n-phenylbenzamides
Shang, Siyun,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 6216 - 6219 (2014/06/23)
Hypervalent-iodine-mediated oxidative coupling of the two aryl groups in either 2-acylamino-N-phenyl-benzamides or 2-hydroxy-N-phenylbenzamides, with concomitant insertion of the ortho-substituted N or O atom into the tether, has been described for the first time. This unusual metal-free rearrangement reaction involves an oxidative C(sp2)?C(sp2) aryl-aryl bond formation, cleavage of a C(sp2)?C(O) bond, and a lactamization/lactonization. Furthermore, unsymmetrical diaryl compounds can be easily obtained by removing the tether within the cyclized product.
Pyrolysis of O-Allyl Salicylic Amides and Esters, and Related Compounds: Foemation of Isoindolones and Phthalides
Black, Michael,Cadogan, J. I. G.,McNab, Hamish
, p. 155 - 160 (2007/10/02)
Flash vacuum pyrolysis of O-allyl salicylic alkylamides and alkyl esters gives isoindolones and phthalides, respectively, in low (20-40percent) yield.The mechanism involves generation of the phenoxyl radical, regiospecific hydrogen-atom transfer from the alkylamide (or alkyl ester) group and cyclization.A similar sequence was observed with thiophenoxyl radicals.
