I just stumbled across a research paper which details a fairly simple, copper-catalyzed oxidation of tetrahydrobetacarbolines with air at room temperature. The reaction was optimized with copper (II) bromide, DMSO as the solvent and the hindered base, DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) - only this latter reagent might be harder to obtain. And maybe bromides aren't so easy to find. Whatever.
Also, it's rather the opposite of our usual goal of obtaining THH
Anyhow, here's the paper:
https://www.ncbi.nlm.nih...pmc/articles/PMC9078326/Quote:Abstract
A mild, efficient and environmentally benign method for synthesis of aromatic β-carbolines via Cu(ii)-catalyzed oxidation of 1,2,3,4-tetrahydro-β-carbolines (THβCs) was developed, in which air (O2) was used as the clean oxidant. This method has advantages such as environmentally friendliness, mildness, very good tolerance of functional groups, high yielding and easy experiment operation. In addition, this new methodology was successfully applied in the efficient and practical total syntheses of β-carboline alkaloids perlolyrine and flazin.
Will copper prove to be a useful catalyst for the hydrogenation of harmaline to THH though?
“There is a way of manipulating matter and energy so as to produce what modern scientists call 'a field of force'. The field acts on the observer and puts him in a privileged position vis-à-vis the universe. From this position he has access to the realities which are ordinarily hidden from us by time and space, matter and energy. This is what we call the Great Work."
― Jacques Bergier, quoting Fulcanelli