Accessing Highly Substituted Indoles via B(C6F5)3-Catalyzed Secondary Alkyl Group Transfer - data

Herein, we report a synthetic method to access a range of highly substituted indoles via the B(C₆F₅)₃-catalyzed transfer of 2º alkyl groups from amines. The transition metal-free catalytic approach has been demonstrated across a broad range of indoles and amine 2º alkyl donors, including various substituents on both reacting components, to access useful C(3)-alkylated indole products. The alkyl transfer process can be performed using Schlenk line techniques in combination with commercially available B(C₆F₅)₃•nH₂O and solvents, which obviates the requirement for specialized equipment (e.g., glove box).

Analysis of reaction products from this methodology resulted in the following data:

1H, 19F and 13C NMR raw data files

IR spectra

High resolution mass spectrometry spectra.