Tryptamine Synthesis by Iron Porphyrin Catalyzed C-H Functionalization of Indoles with Diazoacetonitrile
Tryptamine Synthesis by Iron Porphyrin Catalyzed C-H Functionalization of Indoles with Diazoacetonitrile
复制标题
DOI：
10.1002/anie.201813631
复制
发表时间：
2019-03-11
影响因子：
16.6
通讯作者：
Koenigs, Rene M.
中科院分区：
文献类型：
--
作者：
Hock, Katharina J.;Knorrscheidt, Anja;Koenigs, Rene M.
利用非贵金属催化剂对C-H键进行官能化是开发高效和可持续工艺的重要研究领域。在此，我们描述了铁卟啉催化的重氮乙腈与N-杂环的反应的发展，产生色胺的重要前体，沿着与实验机理研究和概念验证研究的酶促过程与YfeX酶。通过使用容易获得的FeTPPCl，我们实现了吲哚和吲唑杂环的高效C-H官能化。这些转化具有温和的反应条件，优异的产率和广泛的官能团耐受性，可以在克规模上进行，从而提供了一种独特的简化的色胺途径。
The functionalization of C-H bonds with non-precious metal catalysts is an important research area for the development of efficient and sustainable processes. Herein, we describe the development of iron porphyrin catalyzed reactions of diazoacetonitrile with N-heterocycles yielding important precursors of tryptamines, along with experimental mechanistic studies and proof-of-concept studies of an enzymatic process with YfeX enzyme. By using readily available FeTPPCl, we achieved the highly efficient C-H functionalization of indole and indazole heterocycles. These transformations feature mild reaction conditions, excellent yields with broad functional group tolerance, can be conducted on gram scale, and thus provide a unique streamlined access to tryptamines.