Song Wangze, Blaszczyk Stephanie A, Liu Jitian, Wang Shuojin, Tang Weiping
School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, USA.
Org Biomol Chem. 2017 Sep 20;15(36):7490-7504. doi: 10.1039/c7ob01000a.
In carbonylative benzannulations, feedstock carbon monoxide is converted to a benzene ring, which is one of the most fundamentally important and common rings in natural products and pharmaceutical compounds. Carbon monoxide, however, is rather inert in the absence of transition metals. Historically, carbonylative benzannulations have been mediated by stoichiometric chromium and iron in the form of Fischer carbenes. Recently, a number of transition metal-catalyzed carbonylative benzannulations have been developed, and almost all of them involve rhodium catalysts. This review will briefly discuss the mechanism and applications of carbonylative benzannulations involving Fischer carbenes and compare them with the more recent transition metal-catalyzed processes, including [3 + 2 + 1] cycloadditions, [5 + 1] cycloadditions, and other less common cycloadditions.
在羰基化苯并环化反应中,原料一氧化碳被转化为苯环,苯环是天然产物和药物化合物中最基本且常见的环之一。然而,一氧化碳在没有过渡金属的情况下相当惰性。从历史上看,羰基化苯并环化反应是由化学计量的铬和铁以费歇尔卡宾的形式介导的。最近,已经开发了许多过渡金属催化的羰基化苯并环化反应,并且几乎所有这些反应都涉及铑催化剂。本综述将简要讨论涉及费歇尔卡宾的羰基化苯并环化反应的机理和应用,并将它们与最近的过渡金属催化过程进行比较,包括[3 + 2 + 1]环加成、[5 + 1]环加成以及其他不太常见的环加成反应。