Sodium
Name Reactions
Recent Literature
Na-D15, a sodium dispersion reagent with sodium particle size of 5-15 μm, is
a nonpyrophoric reagent that can be handled in air. A broad range of aliphatic
ester substrates were reduced to primary alcohols by Na-D15/i-PrOH with
good yields. The method compares favorably with modern metal hydride reductions
and is much safer and efficient than the traditional Bouveault-Blanc reduction.
J. An, D. N. Work, C. Kenyon, D. J. Procter, J. Org. Chem., 2014,
79, 6743-6747.
Sodium in silica gel (Na-SG) - a safe, free-flowing powder - has been used for
the Bouveault-Blanc reduction of various aliphatic esters. Primary alcohols were
prepared in excellent yield under mild reaction conditions.
B. S. Bodnar, P. F. Vogt, J. Org. Chem., 2009,
74, 2598-2600.
A practical and scalable single electron transfer reduction enables the
reduction and reductive deuteration of tertiary amides in the presence of sodium
dispersions. The chemoselectivity of this method highly depends on the nature of
the proton donor. Whereas the combination of Na/EtOH affords alcohol products,
the use of Na/NaOH/H2O leads to the formation of amines.
B. Zhang, H. Li, Y. Ding, Y. Yan, J. An, J. Org. Chem., 2018, 83,
6006-6014.
A practical and cost-efficient reductive deuteration of nitriles under single-electron
transfer conditions enables the synthesis of α,α-dideuterio amines in
excellent yields using bench stable
and commercially available sodium dispersions and EtOD-d1.
Y. Ding, S. Luo, A. Adijiang, H. Zhao, J. An, J. Org. Chem., 2018, 83,
12269-12274.
Single-electron-transfer conditions using Na/15-crown-5/H2O enable
a reductive cleavage of unactivated carbon-cyano bonds in aliphatic nitriles.
Compared with the Na/NH3 electride system generated under traditional
Birch conditions, this ammonia-free electride system is more practical and
features better reactivity and chemoselectivity.
Y. Ding, S. Luo, L. Ma, J. An, J. Org. Chem., 2019, 84,
15827-15833.
Reduction of stilbenes with Na metal in dry THF allowed easy access to various
1,2-diaryl-1,2-disodiumethanes. These diorganometallic intermediates gave
1,2-diarylethanes upon aqueous work up, or trans-1,2-diaryl-substituted
cyclopentanes by cycloalkylation with 1,3-dichloropropanes.
U. Azzena, G. Dettori, C. Lubinu, A. Mannu, L. Pisano, Tetrahedron, 2005,
61, 8663-8668.
The use of bench-stable sodium dispersions and recoverable 15-crown-5 ether
enables a significantly improved, practical, and chemoselective ammonia-free
Birch reduction of a broad range of aromatic and heteroaromatic compounds in
excellent yields.
P. Lei, Y. Ding, X. Zhang, A. Adijiang, H. Li, Y. Ling, J. An, Org. Lett.,
2018, 20, 3439-3442.
The use of sodium in silica gel enables an efficient synthesis of symmetrical
disulfanes from organic thiocyanates at room temperature. This protocol provides
an attractive alternative to existing methods for the preparation of symmetrical
disulfanes as it avoids the use of foul-smelling thiols.
C. K. Maurya, A. Mazumder, A. Kumar, P. K. Gupta,
Synlett, 2016, 27, 409-411.
Sodium exhibits better efficacy and selectivity than Li and K for converting
Ph3P(O) to Ph2P(OM). A subsequent reaction with alkyl
halides or with aryl halides in the presence of a Pd catalyst provides phosphine
oxides in good to excellent yields.
J.-Q. Zhang, E. Ikawa, H. Fujino, Y. Naganawa, Y. Nakajima, L.-B. Han, J. Org. Chem., 2020, 85, 14166-14173.
Alkali metals promote a general reductive 1,2-diborations and
1,2-dicarbofunctionalizations of alkenes by employing trimethoxyborane and
strained cyclic ethers such as oxirane and oxetane. In addition, unsymmetrical
carbo- or thioborations have been accomplished via treatment with
trimethoxyborane followed by carbon or sulfur electrophiles.
M. Fukazawa, F. Takahashi, K. Nogi, T. Sasamori, H. Yorimitsu,
Org. Lett., 2020, 22, 2303-2307.
