Logeswaran Ravichandran, Jeganmohan Masilamani
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
Org Lett. 2021 Feb 5;23(3):767-771. doi: 10.1021/acs.orglett.0c03981. Epub 2021 Jan 19.
A rhodium(III)-catalyzed aerobic oxidative cross-coupling of acrylamides with unactivated alkenes via vinylic C-H activation has been developed. The present cross-coupling reaction was examined with a variety of differently functionalized acrylamides and unactivated olefins. In these reactions, highly valuable amide-functionalized butadienes were prepared in good to excellent yields. This protocol was also compatible with Weinreb amides. A possible reaction mechanism involving the chelation-assisted vinylic C-H activation via a carboxylate-assisted deprotonation pathway is proposed.
已开发出一种铑（III）催化的丙烯酰胺与未活化烯烃通过乙烯基C-H活化进行的需氧氧化交叉偶联反应。用各种不同功能化的丙烯酰胺和未活化的烯烃对目前的交叉偶联反应进行了研究。在这些反应中，以良好至优异的产率制备了具有高价值的酰胺功能化丁二烯。该方法也与Weinreb酰胺兼容。提出了一种可能的反应机理，该机理涉及通过羧酸盐辅助的去质子化途径进行的螯合辅助乙烯基C-H活化。
