Triphenylphosphine
See also: trimethylphosphine, triethylphosphine
Name Reactions
Recent Literature
A new, mild protocol for deoxygenation of various phosphine oxides with
retention of configuration is described. Mechanistic studies regarding the
oxygen transfer between the starting phosphine oxide and triphenylphosphine
are also presented.
H.-C. Wu, J.-Q. Yu, J. B. Spencer, Org. Lett., 2004, 6, 4675-4678.
A rhodium-catalyzed methylenation-hydrogenation cascade process allows the
homologation of carbonyl compounds to alkanes in high yields.
H. Lebel, C. Ladjel, J. Org. Chem., 2005, 70, 10159-10161.
A reduction of sulfonyl chlorides in the presence of triphenylphosphine in
toluene enables an efficient and convenient method for the synthesis of
arylthiols.
E. V. Bellale, M. K. Chaudhari, K. G. Akamanchi, Synthesis, 2009,
3211-3213.
A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place
in the presence of K2CO3 at 90°C in DMF as solvent. The
coupling mixture is directly treated with NaBH4 or triphenylphosphine
to afford aryl thiols in good to excellent yields. A wide range of substituted
aryl thiols that bear methoxy, hydroxyl, carboxylate, amido, keto, bromo, and
fluoro groups can be synthesized.
Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong, D. Ma, Org. Lett., 2009,
11, 5250-5253.
In the presence of Ph3P and a catalytic amount of Fe(TCP)Cl, ketenes
react with EDA to give allenes in high yields under neutral conditions. By
employing a chiral phosphine, allenes could be synthesized with high
enantioselectivity in good yields.
C.-Y. Li, X.-B. Wang, X.-L. Sun, Y. Tang, J.-C. Zheng, Z.-H. Xu, Y.-G. Zhou,
L.-X. Dai, J. Am. Chem. Soc., 2007,
129, 1494-1495.
Various carboxylic acids were converted into acyl azides in excellent yields in
the presence of trichloroacetonitrile, triphenylphosphine and sodium azide at
room temperature. The reaction allows the preparation of dipeptides without
deprotection or rearrangement during the reaction.
J.-G. Kim, D. O. Jang, Synlett, 2008,
2072-2074.
Treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride,
oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide
in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl
ethers in good yields.
M. N. S. Rad, A. A. Khalafi-Nezhad, F. Karimitabar, S. Behrouz, Synthesis, 2010,
1724-1730.
Alkyl nitrites were prepared in good to excellent yields by treatment of
alcohols and thiols with
triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu4NNO2 in acetonitrile.
This method allows a selective conversion of primary alcohols in the presence of secondary and tertiary alcohols and thiols.
B. Akhlaghinia, A. R. Pourali, Synthesis,
2004, 1747-1749.
A one-step reaction to assemble pyrroles from α,β-unsaturated imines and acid
chlorides is mediated by triphenylphosphine, which eliminates phosphine oxide to
allow cyclization. This reaction has been employed to access broad range of
pyrroles via modulation of the two building blocks and applied as well to the
synthesis of lukianol A.
Y. Lu, B. A. Arndtsen, Org. Lett., 2009,
11, 1369-1372.
A new and efficient three-component reaction between dialkyl
acetylenedicarboxylates, aromatic amines, triphenylphosphine, and arylglyoxals
afforded polysubstituted pyrrole derivatives in high yields. The reactions were
performed in dichloromethane at room temperature and under neutral conditions.
M. Anary-Abbasinejad, K. Charkhati, H. Anaraki-Ardakani, Synlett, 2009,
1115-1117.
A reaction between dialkyl acetylenedicarboxylates and β-aminoketones promoted
by triphenylphosphine allows an efficient one-pot synthesis of polysubstituted
2,5-dihydropyrrole derivatives. The prepared 2,5-dihydropyrroles can be easily
oxidized to the corresponding pyrrole derivatives with chromium trioxide.
M. Anary-Abbasinejad, E. Poorhassan, A. Hassanabadi, Synlett, 2009,
1929-1932.
A novel, efficient, and general domino reaction of 2-acylaziridines with the
Huisgen zwitterions furnishes 2-pyrazolines. A possible mechanism for the domino
sequence is proposed.
S.-L. Cui, J. Wang, Y.-G. Wang, Org. Lett., 2008,
10, 13-16.
In one-pot Wittig olefination reactions of aldehydes, an excess of rasta
resin-PPh3, a heterogeneous polystyrene-based phosphine, was used for
the in situ generation of the phosphorane reactant and enabled the isolation of
a high yield of very pure alkene product after only filtration and solvent
removal. The excellent results obtained in this study are attributed to the
flexible nature of the rasta resin structure.
P. S.-W. Leung, Y. Teng, P. H. Toy, Synlett, 2010,
1997-2001.
A polymer-bound, triphenylphosphine-supported reagent allows a one-pot, two-step
synthesis of secondary amines from the corresponding azide and a reactive alkyl
halide.
S. Ayesa, B. Samuelsson, B. Classon, Synlett, 2008,
89-93.
