Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of Enamines and related compounds
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Recent Literature
A Rh(III)-catalyzed β-C(sp2)-H arylation of various acyclic
enamides with environmentally friendly arylsilanes offers extraordinary efficacy
and stereoselectivity, a wide scope of substrates, and good functional group
tolerance.
X. Jiang, G. Wang, Z. Zheng, X. Yu, Y. Hong, H. Xia, C. Yu, Org. Lett., 2021, 23,
31-36.
An atom-economical iridium-catalyzed asymmetric hydroalkenylation of
α-olefins through directed C-H cleavage of enamides is highly branch-selective
and enantioselective, delivering trisubstituted alkenes with an allylic
stereocenter.
X. Sun, E.-Z. Lin, B.-J. Li, J. Am. Chem. Soc.,
2022, 144, 17351-17358.
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.
N-Tosyl diazoketamines were prepared by addition of the ethyl
α-diazoacetate anion to N-sulfonylimines. A subsequent diazo decomposition of
the diazoketamines with Rh2(OAc)4 as catalyst provided
α-aryl-β-enamino esters in good yields and high stereoselectivity via aryl
migration.
N. Jiang, Z. Qu, J. Wang, Org. Lett., 2001,
3, 2989-2992.