Categories: C-C Bond Formation > Arenes >
Carboxylation, synthesis of benzoates and benzamides
| Related |
|
 |
Name Reactions
Recent Literature
Treatment of 2,2-dimethylpropan-1,3-diol esters of aryl- and alkenylboronic
acids with a catalytic amount of [Rh(OH)(cod)]2 in the presence
of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60°C under carbon
dioxide atmosphere gave carboxylic acids in good yields.
K. Ukai, M. Aoki, J. Takaya, N. Iwasawa, J. Am. Chem. Soc.,
2006,
128, 8706-8707.
An operationally simple hydroxycarbonylation of aryl and vinyl triflates to
the corresponding carboxylic acids with a palladium-mediated microwave
system was carried out in water.
G. Lesma, A. Sacchetti, A. Silvani,
Synthesis, 2006, 594-596.
Sonication of a mixture of magnesium powder, 1,2-dibromoethane, aryl bromide
and diethyl dicarbonate in THF followed by treatment with BF3ˇOEt2
at room temperature afforded aryl ester with reasonable yield. A series of
aryl bromides were investigated and transformed to their corresponding aryl
esters.
A. S.-Y. Lee, C.-C. Wu, L.-S. Lin, H.-F. Hsu, Synthesis, 2004,
568-572.
Regioselective halogen-metal exchange reactions using isopropylmagnesium
chloride were carried out on 3-substituted 1,2-dibromo arenes.
K. Menzel, L. Dimichele, P. Mills, D. E. Frantz, T. D. Nelson, M. H. Kress, Synlett, 2006,
1948-1952.
The Pd-catalyzed coupling of ortho-substituted arylboronic esters
with carbamoyl chlorides gives tertiary benzamides in good yield.
M. Lysen, S. Kelleher, M. Betrup, J. L. Kristensen, J. Org. Chem.,
2005,
70, 5342-5343.
Tertiary amides can be synthesized by a palladium-catalyzed coupling of
N,N-dimethylformamide with aryl or alkenyl halides in the presence of
phosphoryl chloride.
K. Hosoi, K. Nozaki, T. Hiyama, Org. Lett., 2002, 4,
2849-2851.
Cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each
substituted with activating groups, occurred specifically at the acetylenic
center. A remote acrylyl group bound to the olefinic site totally dominated the
regiochemical course of the cycloaddition. Explanations for these findings at
the computational level are provided.
M. Dai, D. Sarlah, M. Yu, S. J. Danishefsky, G. O. Jones, K. N. Houk, J. Am. Chem. Soc., 2007,
129, 645-657.
