Lithium aluminum deuteride is a material applied in isotype labeling, deuterium exchange reactions, deuterium isotope effects, substrate for chemical synthesis (including organometallic compounds).
In isotype labeling, lithium aluminum deuteride(1.0M THF solution; 4.0mL; 4.0mmol) reduce [13C15N]benzo[b]thiophene-3-carbonitrile to give [13CD215N]benzo[b]thiophen-3-yl-methylamine stable isotope-labeled compound with four stable isotope atoms[1]. Lithium aluminum deuteride is also used for novel cage oxaheterocycles synthesis (155mg, 4.08mmol in dry THF (20mL)) and deuterium-labeled analogs of the lipid hydroperoxide-derived bifunctional electrophile 4-oxo-2(*E*)-nonenal synthesis as a deuteride donor[2,3]. The role of lithium aluminum deuteride in the selective deuteration of carbonyl-containing molecules aids in elucidating reaction mechanisms and metabolic pathways.
References:
[1] Lin, Ronghui et al. “Expeditious syntheses of stable and radioactive isotope-labeled anticonvulsant agent, JNJ-26990990, and its metabolites.” *Journal of labelled compounds & radiopharmaceuticals* vol. 56,1 (2013): 22-6. doi:10.1002/jlcr.3013
[2] Marchand, A P et al. “Synthesis of novel cage oxaheterocycles.” *The Journal of organic chemistry*vol. 66,6 (2001): 2072-7. doi:10.1021/jo001611c
[3] Arora, Jasbir S et al. “Synthesis of deuterium-labeled analogs of the lipid hydroperoxide-derived bifunctional electrophile 4-oxo-2(*E*)-nonenal.” *Journal of labelled compounds & radiopharmaceuticals* vol. 54,5 (2011): 247-251. doi:10.1002/jlcr.1860