Ascorbic Acid, Vitamin C
Name Reactions
Recent Literature
Aryl radicals generated in situ from arene diazonium fluoroborates promoted
by ascorbic acid enable a convenient and general oxidative arylation of vinyl
arenes in air at room temperature in the absence of any additive and visible
light irradiation. Various 2-aryl acetophenones have been obtained in good
yields.
B. Majhi, D. Kundu, B. C. Ranu, J. Org. Chem.,
2015,
80, 7739-7745.
A cyanomethyl radical species generated from a cyanomethylphosphonium ylide by
irradiation with visible light in the presence of an iridium complex, a thiol,
and ascorbic acid enables an efficient 1,2-hydro(cyanomethylation) of alkenes.
The cyanomethyl radical species adds across the C=C double bond to form an
elongated alkyl radical species that accepts a hydrogen atom from the thiol.
T. Miura, D. Moriyama, Y. Funakoshi, M. Murakami, Synlett, 2019,
30,
511-514.
In situ nitrosation of anilines followed by reduction with ascorbic acid to form
aryl radicals and thiolation with disulfides provided aryl sulfides. This mild,
metal-free synthesis of aryl sulfides proceeded smoothly without heating or
irradiation. This strategy can be expanded to the synthesis of aryl selenides.
M.-j. Bu, G.-p. Lu, C. Cai,
Synlett, 2015, 26, 1841-1846.
A transition metal/ligand-free disulfuration of anilines can be performed
under mild conditions and exhibits broad scope across the aniline substrate and
disulfur transfer reagent classes (dithiosulfonate or tetrasulfide). This
reaction can be considered as a reductive disulfuration variation of the classic
Sandmeyer reaction.
S. Chen, S. Cao, C. Liu, B. Wang, X. Ren, H. Huang, Z. Peng, X. Wang, Org. Lett., 2021, 23,
7428-7433.
An iridium photocatalyst enables the addition of fluorinated groups to nitrones
using ascorbic acid as a stoichiometric reducing agent. Partially fluorinated
alkyl iodides can also be effectively used. The resulting hydroxylamines can be
readily converted to valuable fluorinated amines by reduction with zinc.
V. I. Supranovich, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett.,
2018, 20, 840-843.
A dual cobalt- and photoredox-catalyzed HAT hydroarylation of alkenes offers
high efficiency in the synthesis of a δ-lactams and various other benzo-fused
hetercycles compared to established protocols. The proposed mechanism is
supported by experiments and DFT calculations.
Y. Yamaguchi, Y. Seino, A. Suzuki, Y. Kamei, T. Yoshino, M. Kojima, S.
Matunaga, Org. Lett.,
2022, 24, 2441-2445.
