Iridium-catalyzed α-selective deuteration of alcohols was written by Itoga, Moeko;Yamanishi, Masako;Udagawa, Taro;Kobayashi, Ayane;Maekawa, Keiko;Takemoto, Yoshiji;Naka, Hiroshi. And the article was included in Chemical Science in 2022.Electric Literature of C7H6Cl2O This article mentions the following:
The α-selective, iridium(III)-bipyridonate-catalyzed hydrogen(H)/deuterium(D) isotope exchange of alcs. using deuterium oxide (D2O) as the primary deuterium source to afford deuterated alcs. RCD2OH [R = Ph, 2-MeC6H4, 4-FC6H4, etc.], R1DCOHR2 [R1 = Ph, 4-ClC6H4, 4-BrC6H4, etc.; R2 = Me, cyclopropyl, Ph] was reported. This method enabled the direct, chemoselective deuteration of primary and secondary alcs. under basic or neutral conditions without being affected by coordinative functional groups such as imidazole and tetrazole. Successful substrates for deuterium labeling include the pharmaceuticals losartan potassium, rapidosept, guaifenesin and diprophylline. The deuterated losartan potassium showedhigher stability toward the metabolism by CYP2C9 than the protiated analog. Kinetic and DFT studies indicated that the direct deuteration proceeded through dehydrogenation of alc. to the carbonyl intermediate, conversion of [IrIII-H] to [IrIII-D] with D2O, and deuteration of the carbonyl intermediate to give the α-deuterated products. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Electric Literature of C7H6Cl2O).
(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Electric Literature of C7H6Cl2O
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts