87842-96-4Relevant articles and documents
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.
RhII-Catalyzed Intermolecular C?H Arylation of Aromatics with Diazo Quinones
Wu, Kai,Cao, Bei,Zhou, Cong-Ying,Che, Chi-Ming
supporting information, p. 4815 - 4819 (2018/03/21)
We developed an efficient synthesis of biaryls by a dirhodium(II)-catalyzed aromatic C?H arylation with diazo quinones. The new biaryl synthesis can be performed under mild and neutral conditions and without directing group chelation assistance. The reaction tolerates various functionalities and is applicable to a broad range of aromatics. The regioselectivity of the C?H arylation was often high and predictable. The synthetic utility of the method was demonstrated by the late-stage modifications of a series of pharmaceuticals and functional materials as well as a short synthesis of a transthyretin amyloid inhibitor.
Cp?Rh(iii) and Cp?Ir(iii)-catalysed redox-neutral C-H arylation with quinone diazides: quick and facile synthesis of arylated phenols
Zhang, Shang-Shi,Jiang, Chun-Yong,Wu, Jia-Qiang,Liu, Xu-Ge,Li, Qingjiang,Huang, Zhi-Shu,Li, Ding,Wang, Honggen
supporting information, p. 10240 - 10243 (2015/06/22)
Cp?Rh(iii)- and Cp?Ir(iii)-catalysed direct C-H arylation with quinone diazides as efficient coupling partners is disclosed. This redox-neutral protocol offers a facile, operationally simple and environmentally benign access to arylated phenols. The reaction represents the first example of Cp?Ir(iii)-catalysed C-H direct arylation reaction.
