53330-45-3Relevant articles and documents
Preparation method of N-acyl indole compound
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Paragraph 0031-0037, (2021/06/06)
The invention discloses a preparation method of an N-acyl indole compound. The preparation method comprises the following steps: adding a palladium catalyst, potassium carbonate, a carbon monoxide substitute, 2-alkynylaniline and an aryl iodide into an or
Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans
Andries-Ulmer, Anna,Brunner, Christoph,Rehbein, Julia,Gulder, Tanja
supporting information, p. 13034 - 13041 (2018/09/27)
Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.
Regioselective Synthesis of 2-Substituted Indoles from Benzotriazoles and Alkynes by Photoinitiated Denitrogenation
Teders, Michael,Pitzer, Lena,Buss, Stefan,Glorius, Frank
, p. 4053 - 4056 (2017/06/19)
Herein, we describe a photoinitiated and regioselective synthesis of 2-substituted indoles under mild reaction conditions. This biologically privileged scaffold was accessed in good yields from N-aroylbenzotriazoles, a quencher class previously identified using our mechanism-based luminescence screening, and terminal alkynes in the presence of a photocatalyst and blue light irradiation. This straightforward protocol displays a broad substrate scope and functional group tolerance. Furthermore, the mildness and robustness of the reaction were assessed by the application of an additive-based robustness screen. The determination of the reaction quantum yield and Stern-Volmer studies support the proposed photoinitiated radical chain mechanism.