Steric, Electronic and Conformational Synergistic Effects in the Au(I)-catalyzed alpha-C-H Bond Functionalization of Tertiary Amines



Direct C-H bond functionalization is a useful strategy for the straightforward formation of C-C and C-Heteroatom bonds. In the present work, a unique approach for the challenging electrophilic Au-catalyzed alpha-C-H bond functionalization of tertiary amines is presented. Electronic, steric and conformational synergistic effects exerted by the use of a malonate unit in the substrate were key to the success of this transformation. This new reactivity was applied to the synthesis of tetrahydro-g-carboline products which, under oxidative conditions, could be converted into valuable structural motifs found in bioactive alkaloid natural products


Thumbnail image of Manuscript Az C-H ChemXRiv.pdf

Supplementary material

Thumbnail image of SI1 Az C-H Procedures Characterization.pdf
Procedures & Characterizations
Detailed synthetic procedures / Optimization of catalytic system / Compound description / DFT data
Thumbnail image of SI2 Az C-H NMR.pdf
NMR spectra
NMR spectra of substrates & products