C-H and C-C Functionalization of Ketones

报告题目:C-H and C-C Functionalization of Ketones

报告时间:2019年3月21日下午4:00

报告地点:仲英楼B251

报告人:董广彬 教授

报告人简介:

董广彬教授，2003年在北京大学获得学士学位之后，2009年在美国斯坦福大学获得博士学位，师从Barry M. Trost教授。2009年到2011年在美国加州理工学院从事博士后研究，师从诺贝尔奖得主Robert H. Grubbs教授。2011年于美国德克萨斯大学奥斯丁分校成为助理教授后，5年时间越级升为正教授。2016年起，迁到美国芝加哥大学。独立工作以来，已先后在Nature, Science, Nat. Chem., J. Am. Chem. Soc., Angew. Chem. Int. Ed.等国际顶尖期刊发表近百篇论文

报告摘要：

C-H and C-C bonds are the most abundant bonds in majority of organic compounds. Selective functionalization of C-C and C-H bonds would lead to efficient synthesis of complex target molecules, but these transformations are generally of significant challenges. In the past, we have been focusing on a "cut and sew" strategy to synthesize bridged and fused rings by utilizing metal-catalyzed C-C bond activation of four-membered ketones. Driven by an objective to develop a “cut and sew” reaction with five-membered ring ketones, we obtained an unexpected discovery and later developed a regioselective ketone α-alkylation reaction using simple olefins. This reaction can be further extended to the intramolecular transformation, a formal Conia-Ene reaction, as well as intermolecular alkenylation with alkynes. Meanwhile, driven by the need to improve the efficiency of the ketone alkylation reaction, we accidentally discovered an approach for catalytic C-C bond activation of cyclopentanones and some cyclohexanones, in which the proximal α C-C bond was cleaved and subsequently coupled with a β-aryl group through C-H activation. More recently, activation of the distal C-C bond in these unstrained ketones was enabled through using a bulkier catalyst system