含氟烷基羰基吲哚的可调分子编辑，这一成果由东北师范大学Xihe Bi研究小组经过不懈努力而取得。相关论文于2024年3月5日发表在《自然-化学》杂志上。

在该研究中，研究小组报道了一种由卡宾引发的吲哚的化学发散分子编辑，通过捕获由氟烷基N-triftosylhydrazone原位生成的亲电氟烷基卡宾，可以对分子骨架和外周进行编辑。通过可调的吲哚骨架或外围化学选择性编辑反应，包括单碳插入、C3 gem-二氟烯烃化、串联环丙烷化和N1 gem-二氟烯烃化以及环丙烷化，可以有效地制备出多种含氟N-杂环支架。

通过以可控和化学选择性的方式修饰天然产物的骨架或外围，这种化学发散分子编辑策略的力量得到了强调。团队还从实验和理论两方面，探讨了化学选择性和区域选择性的反应机理和来源。

据了解，通过精确的外周和骨架修饰，从简单的原料构建分子复杂性是现代有机合成的核心。然而，尽管有可能最大限度地提高结构多样性和应用价值，但一种可以通过共同底物修饰芳香族杂环的核心骨架，和外围结构的可控策略仍然是未知的。

附：英文原文

Title: Tunable molecular editing of indoles with fluoroalkyl carbenes

Author: Liu, Shaopeng, Yang, Yong, Song, Qingmin, Liu, Zhaohong, Lu, Ying, Wang, Zhanjing, Sivaguru, Paramasivam, Bi, Xihe

Issue&Volume: 2024-03-05

Abstract: Building molecular complexity from simple feedstocks through precise peripheral and skeletal modifications is central to modern organic synthesis. Nevertheless, a controllable strategy through which both the core skeleton and the periphery of an aromatic heterocycle can be modified with a common substrate remains elusive, despite its potential to maximize structural diversity and applications. Here we report a carbene-initiated chemodivergent molecular editing of indoles that allows both skeletal and peripheral editing by trapping an electrophilic fluoroalkyl carbene generated in situ from fluoroalkyl N-triftosylhydrazones. A variety of fluorine-containing N-heterocyclic scaffolds have been efficiently achieved through tunable chemoselective editing reactions at the skeleton or periphery of indoles, including one-carbon insertion, C3 gem-difluoroolefination, tandem cyclopropanation and N1 gem-difluoroolefination, and cyclopropanation. The power of this chemodivergent molecular editing strategy has been highlighted through the modification of the skeleton or periphery of natural products in a controllable and chemoselective manner. The reaction mechanism and origins of the chemo- and regioselectivity have been probed by both experimental and theoretical methods.

DOI: 10.1038/s41557-024-01468-2

Source: https://www.nature.com/articles/s41557-024-01468-2