DIPHENYL-2,2',4,4',6,6'-D6-AMINE synthesis

Yield:99234-91-0 96%

Reaction Conditions:

with hydrogen;water-d2 at 120; under 15001.5 Torr; for 24 h;Autoclave;regioselective reaction;

Steps:

General procedure for the deuteration reactions.

General procedure: In a 4 ml vial fitted with a magnetic stir bar and septum cap, iron catalyst (60 mg, 20 mol%) and substrate (0.25 mmol) were added. Then, a needle was inserted in the septum, allowing gaseous reagents to enter. After adding the solvent deuterium oxide (1.5 ml), the vials (up to eight) were set in an alloy plate and then placed into a 300 ml steel Parr autoclave. The autoclave was flushed with hydrogen six times at 10 bar and finally pressurized to the desired value (20 bar). Then, it was placed into an aluminium block and heated to the desired temperature. At the end of the reaction, the autoclave was quickly cooled down to r.t. with an ice bath and vented. Finally, the samples were removed from the autoclave, and ethyl acetate was added to the crude mixture. This mixture was centrifuged, and the organic layer was removed from the vials (three times). After removal of all volatiles in vacuo, the desired products were obtained. In case of anilines with deuterium labelling on the nitrogen, 1 ml H₂O was added during work up and N-D was replaced by N-H.

References:

Li, Wu;Rabeah, Jabor;Bourriquen, Florian;Yang, Dali;Kreyenschulte, Carsten;Rockstroh, Nils;Lund, Henrik;Bartling, Stephan;Surkus, Annette-Enrica;Junge, Kathrin;Brückner, Angelika;Lei, Aiwen;Beller, Matthias [Nature Chemistry,2022,vol. 14,# 3,p. 334 - 341]