Extended Data Fig. 4: Screening of catalytic reactions for alkene perdeuteration.
From: Hydrogenative alkene perdeuteration aided by a transient cooperative ligand
a, Screening of different thiols. Various thiol TCLs exert different effects on the H/D exchange between D2O and H2, as well as alkene perdeuteration, due to differences in their electronic and steric properties. Consequently, different thiols lead to varying deuteration results, with cyHexSH providing the best result of all examined thiols. b, Compatibility of the catalytic system with different functional groups that are frequently found in bioactive molecules and pharmaceuticals (active protons were not taken into consideration in evaluating additive recovery). Some strongly-coordinating N-donors, that is, benzylamine, pyridine and phenylpropionitrile, showed detrimental effects, but even in these cases good product yields were obtained (71%–83%), and deuterium incorporation remained high. Among the studied additives, only benzoic acid completely halted the catalytic activity. This may be due to deactivation of the catalyst by formation of a stable ruthenium-carboxylate species, as has been previously observed (ref. 25). c, Optimization of catalytic conditions.
