7374-34-7Relevant academic research and scientific papers
Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
Che, Chi-Ming,Wu, Kai,Wu, Liang-Liang,Zhou, Cong-Ying
supporting information, p. 16202 - 16208 (2020/07/17)
A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.
A New Route for the Synthesis of 2-Amino-biphenyls Involving Enamine Rearrangement of Pyridinium Salts
Fadda, A. A.,El-Morsy, S. S.
, p. 361 - 363 (2007/10/02)
2-Benzyl-1-methylpyridinium iodides (IIa-c) undergo ring opening and recyclization reactions when heated with aq. sodium hydroxide to give 2-methylaminobiphenyls (IIIa-c).The effect of aq. alkylamine and alkylammonium sulphite solution on this type of reaction has also been studied.
