295778-50-6Relevant academic research and scientific papers
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.
Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles
Montgomery, Thomas D.,Zhu, Ye,Kagawa, Natsuko,Rawal, Viresh H.
supporting information, p. 1140 - 1143 (2013/03/29)
A set of general methods for the palladium-catalyzed decarboxylative C3-allylation and C3-benzylation of indoles, starting from the corresponding N-alloc and N-Cbz indoles, respectively, is reported. This chemistry provides ready access to a wide range of
