Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.
IITB-Monash Research Academy, Near estate office, IIT Bombay Powai, Mumbai, 400076, India.
Chemistry. 2020 Sep 4;26(50):11558-11564. doi: 10.1002/chem.202001368. Epub 2020 Aug 11.
The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work, we demonstrate the para-selective introduction of versatile nitrile moiety, enabled by a detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.
选择性功能化的意义在于其具有优越的选择性、易于合成和多样化的产物用途。在这项工作中，我们展示了通过可分离和可重复使用的氢键辅助基团，实现了多功能腈基的对位选择性引入。该方法无论底物的电子偏向如何都能保持其效率。通过实验和计算机械工具探测到了步骤能量的明显变化，预示着对位氘化的开始。该方法的合成影响通过导向基团的可重复使用和后合成修饰得到了强调。
