Mild and selective hydrogen-deuterium exchange for aromatic hydrogen of amines.
aralkyl amines
aromatic amines
deuterated Trifluoromethanesulfonic acid
hydrogen-deuterium exchange
Journal
Journal of labelled compounds & radiopharmaceuticals
ISSN: 1099-1344
Titre abrégé: J Labelled Comp Radiopharm
Pays: England
ID NLM: 7610510
Informations de publication
Date de publication:
08 2023
08 2023
Historique:
revised:
26
05
2023
received:
03
04
2023
accepted:
30
05
2023
medline:
10
8
2023
pubmed:
20
6
2023
entrez:
20
6
2023
Statut:
ppublish
Résumé
The direct electrophilic deuteration of the aromatic moiety in aromatic and aralkyl amines is reported. The acid-catalyzed deuteration is facilitated by deuterated trifluoromethanesulfonic acid, [D]triflic acid, CF
Substances chimiques
Hydrogen
7YNJ3PO35Z
Deuterium
AR09D82C7G
Amines
0
trifluoromethanesulfonic acid
JE2SY203E8
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
321-331Informations de copyright
© 2023 John Wiley & Sons Ltd.
Références
Liu JF, Harbeson SL, Brummel CL, Tung R, Silverman R, Doller D. Annual Reports in Medicinal Chemistry. Academic Press-Elsevier; 2017. 519 p.
Chatterjee B, Krishnakumar V, Gunanathan C. Selective α-deuteration of amines and amino acids using D2O. Org Lett. 2016;18(22):5892-5895. doi:10.1021/acs.orglett.6b02978
Kselíková V, Vítová M, Bišová K. Deuterium and its impact on living organisms. Folia Microbiol. 2019;64(5):673-681. doi:10.1007/s12223-019-00740-0
Atzrodt J, Derdau V, Fey T, Zimmermann J. The renaissance of H/D exchange. Angew Chem Int Ed. 2007;46(41):7744-7765. doi:10.1002/anie.200700039
Pirrone GF, Iacob RE, Engen JR. Applications of hydrogen/deuterium exchange MS from 2012 to 2014. Anal Chem. 2015;87(1):99-118. doi:10.1021/ac5040242
Michelotti A, Roche M. 40 Years of hydrogen-deuterium exchange adjacent to heteroatoms: a survey. Synthesis. 2019;51(06):1319-1328. doi:10.1055/s-0037-1610405
Atzrodt J, Derdau V, Kerr WJ, Reid M. C−H functionalisation for hydrogen isotope exchange. Angew Chem Int Ed. 2018;57(12):3022-3047. doi:10.1002/anie.201708903
Orchin M, Bollinger DM. Biochemistry. Structure and Bonding. Springer; 2007. 167 p.
Yang X, Ben H, Ragauskas AJ. Recent advances in the synthesis of deuterium-labeled compounds. Asian J Org Chem. 2021;10(10):2473-2485. doi:10.1002/ajoc.202100381
Wang L, Murai Y, Yoshida T, et al. Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid. Biosci Biotechnol Biochem. 2014;78(7):1129-1134. doi:10.1080/09168451.2014.917267
Giles R, Lee A, Jung E, Kang A, Jung KW. Hydrogen-deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid. Tetrahedron Lett. 2015;56(5):747-749. doi:10.1016/j.tetlet.2014.12.102
Giles R, Ahn G, Jung KW. H-D exchange in deuterated trifluoroacetic acid via ligand-directed NHC-palladium catalysis: a powerful method for deuteration of aromatic ketones, amides, and amino acids. Tetrahedron Lett. 2015;56(45):6231-6235. doi:10.1016/j.tetlet.2015.09.100
Akiyama T, Mori K. Stronger Brønsted acids: recent progress. Chem Rev. 2015;115(17):9277-9306. doi:10.1021/acs.chemrev.5b00041
Howells RD, Mc Cown JD. Trifluoromethanesulfonic acid and derivatives. Chem Rev. 1977;77(1):69-92. doi:10.1021/cr60305a005
Tachrim ZP, Wang L, Murai Y, et al. Trifluoromethanesulfonic acid as acylation catalyst: special feature for C- and/or O-acylation reactions. Catalysts. 2017;7(12):40-68. doi:10.3390/catal7020040
Haszeldine RN, Kidd JM. Perfluoroalkyl derivatives of Sulphur. Part I. Trifluoromethanesulphonic acid. J Chem Soc. 1954;4228-4232. doi:10.1039/jr9540004228
Murai Y, Wang L, Masuda K, et al. Rapid and controllable hydrogen/deuterium exchange on aromatic rings of α -amino acids and peptides. Eur J Org Chem. 2013;2013(23):5111-5116. doi:10.1002/ejoc.201300405
Zhang W, Tachrim ZP, Tokoro Y, et al. Hydrogen-deuterium exchange of indole-3-propionic acid with deuterated trifluoromethanesulfonic acid. ARKIVOC. 2023;2022(9):33-39. doi:10.24820/ark.5550190.p011.836
Hashimoto M, Puteri Tachrim Z, Nakagawa S, et al. Synthesis of deuterated cyclodopa with hydrogen/deuterium exchange. Heterocycles. 2019;99(1):404-414. doi:10.3987/COM-18-S(F)33
Hashimoto M, Puteri Tachrim Z, Kurokawa N, Tokoro Y. Hydrogen-deuterium exchange of histidine and histamine with deuterated trifluoromethanesulfonic acid. Heterocycles. 2020;101(1):357-362. doi:10.3987/COM-19-S(F)28
Appert E, Martin-Mingot A, Karam O, et al. Superacid-mediated late-stage aromatic polydeuteration of pharmaceuticals. Chem - a Eur J. 2022;28(49):e202201583. doi:10.1002/chem.202201583
Zaitsev VG, Daugulis O. Catalytic coupling of haloolefins with anilides. J am Chem Soc. 2005;127(12):4156-4157.
Hesk D, das PR, Evans B. Deuteration of acetanilides and other substituted aromatics using [Ir (COD)(Cy3P)(Py)]PF6 as catalyst. J Label Compd Radiopharm. 1995;36(5):497-502. doi:10.1002/jlcr.2580360514
Sawama Y, Nakano A, Matsuda T, Kawajiri T, Yamada T, Sajiki H. H−D exchange deuteration of arenes at room temperature. Org Process Res Dev. 2019;23(4):648-653. doi:10.1021/acs.oprd.8b00383
Wang W, Fang Y, Hong T. A kind of preparation method of stable isotope labeling 6-benzyladenine internal standard reagent. Patent CN 109305968 A, 2019.
Lockley WJS. Hydrogen isotope labelling using iridium(I) dionates. J Label Compd Radiopharm. 2010;53(11-12):668-673. doi:10.1002/jlcr.1806
McAuley B, Hickey MJ, Kingston LP, et al. Convenient and efficient deuteration of functionalized aromatics with deuterium oxide: catalysis by cycloocta-1,5-dienyliridium(I) 1,3-dionates. J Label Compd Radiopharm. 2003;46(13):1191-1204. doi:10.1002/jlcr.780
Garman RN, Hickey MJ, Kingston LP, et al. Labelling of anilines, benzylamines and some N-heterocyclics using cycloocta-1, 5-dienyliridium (I)-1, 1, 1, 5, 5, 5-hexafluoro-pentan-2, 4-dionate and isotopic hydrogen gas in DMF or DMA. J Label Compd Radiopharm. 2005;48(1):75-84. doi:10.1002/jlcr.898
Hickey MJ, Jones JR, Kingston LP, et al. Iridium-catalysed labelling of anilines, benzylamines and nitrogen heterocycles using deuterium gas and cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate. Tetrahedron Lett. 2003;44(20):3959-3961. doi:10.1016/S0040-4039(03)00750-0
Pedras MSC, To QH. Synthesis of stable isotope-labeled nasturlexins and potential precursors to probe biosynthetic pathways of cruciferous phytoalexins. J Label Compd Radiopharm. 2018;61(2):94-106. doi:10.1002/jlcr.3591
Ingold CK, Raisin CG, Wilson CL, Bailey CR, Topley B. Structure of benzene. Part II. Direct introduction of deuterium into benzene and the physical properties of hexadeuterobenzene. J Chem Soc. 1936;915-925. doi:10.1039/jr9360000915
Tice BBP, Lee I, Kendall FH. Kinetic studies of hydrogen exchange in dialkylanilines. II. J am Chem Soc. 1966;88(16):3813-3819. doi:10.1021/ja00968a025
Shao C. Deuterated benzyl pyrimidinedione derivative and its application, Patent CN 111116492 A, 2020.
Kobayashi Y, Hayashi N, Tan C, Kishi Y. Toward the creation of NMR databases in chiral solvents for assignments of relative and absolute stereochemistry: proof of concept. Org Lett. 2001;3(14):2245-2248. doi:10.1021/ol010108z
Kopecky KR, Evani S. Mechanism of initiation in the thermal polymerization of styrene. Kinetic deuterium isotope effects in the initiation step of the thermal polymerization of some deuterated styrenes. Can J Chem. 1969;47(21):4049-4058. doi:10.1139/v69-671