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US 12,735,369 B2Granted
Selective transition metal catalyzed deuterium incorporation into alkyne and alkene functionalities
AssigneeMarquette University
InventorsJoseph R. Clark, Zoua Pa Vang, Mitchell Mills, Albert Reyes, Samantha E. Sloane, Emanuel Rivera Torres
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Abstract
Disclosed herein are deuterated compounds and transition metal catalyzed methods for making deuterated compounds. The disclosed methods are regioselective and enantioselective and may be utilized to prepare isomerically and/or enantiomerically pure or enriched deuterated compounds. The disclosed methods also may be modified in order to prepared fluorinated compounds.
Claims10
A method for preparing a deuterated compound, the method comprising reacting a reaction mixture comprising:
- (i) a substrate compound comprising an alkyne functionality or an alkene functionality;
- (ii) a transition metal catalyst;
- (iii) a phosphine ligand for the transition metal catalyst, wherein the phosphine ligand is (R)-(−)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole, (S)-(−)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole, or 1,2-bis(bis(3,5-di-tert-butylphenyl)phosphino)benzene;
- (iv) a substituted silane comprising a donor hydrogen atom or a donor deuterium atom;
- (v) D2O or an alcohol comprising a donor hydrogen atom or a donor deuterium atom;
- and
- (vi) a solvent;
- wherein the reaction mixture is reacted under conditions such that the alkyne functionality or the alkene functionality of the substrate compound is reductively deuterated to a deuterated alkane functionality to provide the deuterated compound.
5 more elements
Dependencies are inferred from the claim text.