Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Enamines and related compounds
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Recent Literature
Arylations of electron-rich heteroatom-substituted olefins were performed
with electron-rich arylboronic acids via palladium(II) catalysis. This mild
protocol, which offers access to functionalized enamides, exploits oxygen gas
for reoxidation and a stable 1,10-phenanthroline bidentate ligand to promote the
palladium(II) regeneration and to control the regioselectivity.
M. M. S. Andappan, P. Nilsson, H. v. Schenck, M. Larhed, J. Org.
Chem., 2004,
69, 5212-5218.
A highly efficient and stereoselective arylation of in situ-generated
azavinyl carbenes affords 2,2-diaryl enamines at ambient temperatures. These
transition-metal carbenes are directly produced from readily available and
stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate
catalyst. In several cases, the enamines can be cyclized into substituted
indoles employing copper catalysis.
N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc., 2012,
134, 14670-14673.
An earth-abundant iron catalyst enables a dehydrogenative acylation of enamides
with aldehydes to provide valuable β-ketoenamides with excellent functional group tolerance.
The C-H acylation occurs with absolute Z-selectivity.
R.-H. Liu, Z.-Y. Shen, C. Wang, T.-P. Loh, X.-H. Hu,
Org. Lett., 2020, 22, 944-949.
A Rh(III)-catalyzed protocol for the amidation of anilide and enamide C-H bonds
with isocyanates provides direct and efficient syntheses of N-acyl
anthranilamides, enamine amides, and pyrimidin-4-one heterocycles.
K. D. Hesp, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc., 2011,
133, 11430-11433.
An efficient, mild, and general method for the C-arylation of β-enamino
esters and ketones with arynes provides a facile and direct access to various
substituted aromatic β-enamino compounds in good yield.
Y. K. Ramtohul, A. Chartrand, Org. Lett., 2007,
9, 1029-1032.