Categories: C-C Bond Formation > Arenes >
Formylation, synthesis of benzaldehydes
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Recent Literature
A ligandless palladium-catalyzed reductive carbonylation of aryl iodides for the
synthesis of aromatic aldehydes proceeded effectively even under ambient
temperature and pressure.
W. Han, B. Liu, J. Chen, Q. Zhou,
Synlett, 2017, 28, 835-840.
A palladium-catalyzed formylation of aryl halides with isocyanide in the
presence of Et3SiH provides important aldehydes in good yield. This
reaction offers mild conditions, convenient operation, low toxicity, and wide
functional group tolerance.
X. Jiang, J.-M. Wang, Y. Zhang, Z. Chen, Y.-M. Zhu, S.-J. Ji, Org. Lett., 2014,
16, 3492-3495.
The combination of Pd(PCy3)2Cl2 and
di-2-pyridyl ketone catalyzes a reductive formylation of aryl iodides with
carbon dioxide as the carbonyl source under mild reaction conditions in the
presence of phenylsilane as the reductive reagent. This convenient reaction
provides a variety of aromatic aldehydes in good yields with wide substrate
scope and good functional group tolerance.
D. Li, L. Wei, W. Xiong, H. Jiang, C. Qi, J. Org. Chem., 2023, 88,
5231-5237.
A palladium-catalyzed reductive carbonylation enables a facile and practical
synthesis of aromatic aldehydes from aryl iodides and HCOOH. HCOOH serves not
only as convenient and environmental-friendly C1 source but also as the reviving
agent in the reductive elimination process of a Pd-catalyst.
G. Sun, X. Lv, M. Lei, L. Hu, Org. Lett.,
2017, 19, 4235-4238.
O-Aryl N-isopropylcarbamates, conveniently prepared from
phenols and isopropyl isocyanate, are subjected to an efficient ortho-lithiation
protocol to afford the corresponding salicylaldehydes in a one-pot operation
in high yields.
M. Kauch, D. Hoppe,
Synthesis, 2006, 1575-1577.
Reaction of nitroarenes with tris(benzotriazol-1-yl)methyl anion followed by
treatment with zinc bromide and hydrochloric acid yielded the corresponding p-nitroarylaldehydes in good to excellent yields.
A. R. Katritzky, L. Xie, Tetrahedron Lett., 1996,
37, 347-350.
An efficient iron-catalyzed C3-selective formylation of free or N-substituted
provides 3-formylindoles in good yields in fairly short reaction times in the
presence of formaldehyde and aqueous ammonia, with air as the oxidant. Moreover,
this catalytic formylation of indoles can be applied to gram-scale syntheses.
Q.-D. Wang, B. Zhou, J.-M. Yang, D. Fang, J. Ren, B.-B. Zeng,
Synlett, 2017, 28, 2670-2674.
Eosin Y catalyzes a visible-light-mediated C-3 formylation of indole in the
presence of tetramethylethylenediamine as a carbon source and air as an oxidant
under mild conditions. This protocol tolerates a broad range of functional
groups and provides 3-formylated indoles with good yields.
Y. Zhao, H. Li, S. Yin, Y. Wu, G. Ni, Synlett, 2022,
33,
659-663.
A direct metal- and oxidant-free photochemical decarboxylative formylation of
indoles with 50% aqueous glyoxylic acid proceeds in good yields.
V. Dinesh, R. Nagarajan, Synlett, 2023,
34,
855-857.
An electrochemical hydrogen atom transfer (HAT) strategy enables a C(sp2)-H
formylation of electron-deficient quinolines and isoquinolines using methanol as
a formyl source with a catalytic amount of N-hydroxyphthalimide (NHPI) as
hydrogen atom transfer (HAT) catalyst. This transition-metal and oxidant-free
method could also be applied to the direct C(sp2)-H acetylation or
propionylation.
Y. Liao, C. Jiang, C. Qiang, P. Liu, P. Sun, Org. Lett., 2023, 25,
7327-7331.