Protecting Group-Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions
Protecting Group-Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions
复制标题
DOI：
10.1021/acs.joc.9b03322
复制
发表时间：
2020-06-05
影响因子：
3.6
通讯作者：
Cobb, Steven L.
中科院分区：
文献类型：
--
作者：
Brittain, William D. G.;Cobb, Steven L.
能够利用保护基团来影响远程区域控制，为指导复杂有机分子的后期功能化提供了一种简单的替代方法。然而，文献中并没有广泛报道保护基团对远离其局部化学环境的反应区域选择性有影响的能力。在此，我们报道了远程区域选择性亲电芳香取代（SEAr）反应的发展，该反应是通过应用四氟吡啶（TFP）酚保护基团实现的。我们证明，通过顺序反应和TFP基团的保护/去保护，可以很容易地获得不符合经典SEAr区域选择性规则的取代模式。
Being able to utilize a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalization of complex organic molecules. However, protecting groups that have the ability to influence reaction regioselectivity remote to their local chemical environment are not widely reported in the literature. Herein, we report the development of remote regioselective electrophilic aromatic substitution (SEAr) reactions that are enabled via the application of the tetrafluoropyridyl (TFP) phenol-protecting group. We demonstrate that through sequential reactions and protection/deprotection of the TFP group, substitution patterns that do not conform to classical SEAr regioselectivity rules can be readily accessed.