Deuterated benzylbenzene derivatives and methods of use

A composition comprising a compound having the structure:

• or any diastereomer, tautomer, or isomer thereof, or any pharmaceutically acceptable prodrug, salt, or solvate thereof, wherein
• each R1, R2, R3, R4 and R5 is, independently, —H, -D, a substituent that is optionally deuterated, or group Q:
• A is selected from the group consisting of oxygen and a single bond;
• G is selected from the group consisting of:
• each R6, R7, R8, R9, R10, R14, R15, R16, R19, and R21, is, independently, —H, -D, or a substituent that is optionally deuterated;
• and
• each R11, R12, R13, R17, R18, R20, and R22 is, independently, —H, -D, or halogen;
• wherein
• one of R1, R2, R3, R4, and R5 is group Q;
• R23 is CH2, NH, O, or S;
• and
• at least one of R1-R23 is -D or comprises -D, wherein said composition has an isotopic enrichment factor for deuterium of at least 5.

A method of enriching the deuterium content of a diarylmethylene compound, wherein said method comprises

• (a) combining:
• i. a diarylmethylene compound having a structure according to
• wherein R′ is H or D, and each Ar1 and Ar2 is, independently, an optionally substituted aryl group;
• and
• ii. a mixture comprising deuterium oxide and sodium hydride;
• and
• iii. a phase-transfer catalyst;
• wherein the combination of reagents (i), (ii), and (iii) results in the incorporation of deuterium at the methylene bridge of said diarylmethylene compound;
• and
• (b) optionally combining the product obtained in step (a) one or more times with the reagents (ii) and (iii).