Pang Binghan, Wang Yangyang, Hao Liqiang, Wu Gaorong, Ma Zhihong, Ji Yafei
Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
Biotalk Co., LTD, Shanghai 200092, China.
J Org Chem. 2023 Jan 6;88(1):143-153. doi: 10.1021/acs.joc.2c02006. Epub 2022 Dec 23.
An efficient method of Rh(III)-catalyzed coupling reaction between 2-arylquinazolinones and -difluorostyrenes has been developed. In this work, two diverse structures of monofluoroalkenes and isoindolo[1,2-]quinazolin-10(12)-one derivatives were respectively synthesized by controlling the amount of additives (Ca(OH) and AgNTf) to achieve controlled stepwise breaking of the C-F bonds of -difluorostyrenes. This reaction has the characteristics of a wide range of substrates and good functional group tolerance. Meanwhile, several control experiments were conducted and a plausible mechanism was proposed.
已开发出一种铑(III)催化的2-芳基喹唑啉酮与二氟苯乙烯之间的偶联反应的有效方法。在这项工作中,通过控制添加剂(Ca(OH) 和AgNTf)的量,分别合成了两种不同结构的单氟烯烃和异吲哚并[1,2-a]喹唑啉-10(12)-酮衍生物,以实现二氟苯乙烯C-F键的可控逐步断裂。该反应具有底物范围广和官能团耐受性好的特点。同时,进行了几项对照实验并提出了一个合理的机理。