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.
Claims27
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;
- (iv) a substituted silane comprising a donor hydrogen atom or a donor deuterium atom;
- (v) 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 provide the deuterated compound.
-12. (canceled)
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-20. (canceled)
A compound of any of the following formulas:
- wherein Ar is aryl such as an aromatic carbocycle and/or an aromatic heterocycle optionally substituted at one or more positions with a substituent selected from alkyl, carbonyl, carboxy alkyl ester, phenyl, phenyoxy, halogen, nitro, sulfonamide, pyridinyl, imidazolyl, morpholino, boronic acid, piperidinyl, pyrazolyl, piperazinyl, and tosyl;
- R1, R2, R3, R4, R5, R6, R7, and R8 are independently selected from hydrogen, deuterium, alkyl, and Ar optionally substituted with amino, nitro, hydroxyl, alkoxy, carboxyl, —C(O)—O—R13 where R13 is alkyl, —C(O)—R14 wherein R14 is alkyl, C(R15)(R16)-R17 wherein R15 and R16 are alkoxy, alkylthiol, sulfonamide, or Ar, and R17 is alkyl, or —CH2C(OR18)—R19 wherein R18 and R19 are hydrogen or alkyl;
- and R9, R10, R11, and R12 are independently selected from hydrogen, deuterium, alkyl.
-26. (canceled)
A method for preparing a fluorinated 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;
- (iv) a substituted silane comprising a donor hydrogen atom;
- (v) a fluorine donor compound;
- 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 fluorinated to provide the fluorinated compound.
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-41. (canceled)
Dependencies are inferred from the claim text.