117788-15-5Relevant articles and documents
Traceless directing strategy: Efficient synthesis of N-alkyl indoles via redox-neutral C-H activation
Wang, Chengming,Huang, Yong
, p. 5294 - 5297 (2013)
A general protocol for the synthesis of N-alkyl indoles has been developed via a redox neutral C-H activation strategy using a traceless nitroso directing group. A broad scope of substituted N-alkyl indoles has been prepared in good to excellent yields using a very simple Rh catalyst system in the absence of an external oxidant or any other additive. Good to excellent regioselectivity has been achieved for asymmetrically disubstituted acetylenes.
Assembly of Indole Cores through a Palladium-Catalyzed Metathesis of Ar-X σ-Bonds
Ferrier, Robert C.,Ghasemi, Mehran,Habibi, Azizollah,Jafarpour, Farnaz,Navid, Hamed,Rajai-Daryasarei, Saideh,Safaie, Niloofar
supporting information, p. 9556 - 9561 (2020/12/21)
We describe the development of a new method for construction of highly substituted indole scaffolds through the strategic utilizing of the metathesis of Ar-X σ-bonds based on the dynamic nature of palladium-based oxidative addition/reductive elimination. A suitable and simple catalytic system has provided an appropriate platform for a productive ligand exchange and consecutive carbopalladation/C-H activation/amination of phosphine ligands with alkynes and aromatic/aliphatic amines for construction of structurally diverse indoles.
Predicting the Outcome of Photocyclisation Reactions: A Joint Experimental and Computational Investigation
Wonanke, A. D. Dinga,Ferguson, Jayne L.,Fitchett, Christopher M.,Crittenden, Deborah L.
, p. 1293 - 1303 (2019/02/25)
Photochemical oxidative cyclodehydrogenation reactions are a versatile class of aromatic ring-forming reactions. They are tolerant to functional group substitution and heteroatom inclusion, so can be used to form a diverse range of extended polyaromatic systems by fusing existing ring substituents. However, despite their undoubted synthetic utility, there are no existing models—computational or heuristic—that predict the outcome of photocyclisation reactions across all possible classes of reactants. This can be traced back to the fact that “negative” results are rarely published in the synthetic literature and the lack of a general conceptual framework for understanding how photoexcitation affects reactivity. In this work, we address both of these issues. We present experimental data for a series of aromatically substituted pyrroles and indoles, and show that quantifying induced atomic forces upon photoexcitation provides a powerful predictive model for determining whether a given reactant will photoplanarise and hence proceed to photocyclised product under appropriate reaction conditions. The propensity of a molecule to photoplanarise is related to localised changes in charge distribution around the putative forming ring upon photoexcitation. This is promoted by asymmetry in molecular structures and/or charge distributions, inclusion of heteroatoms and ethylene bridging and well-separated or isolated photocyclisation sites.
