Categories: C=O Bond Formation > Synthesis of ketones >
Synthesis of ketones by derivatisation (hydration) of alkynes
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A highly efficient [(NHC)AuCl]-based catalytic system allows the hydration of
terminal and internal alkynes possessing any combination of alkyl and aryl
substituents under acid-free conditions and at very low catalyst loadings.
N. Marion, R. S. Ramón, S. P. Nolan, J. Am. Chem. Soc., 2009,
131, 448-449.
Activated pyridine borane complexes (Py·BH2X) are capable of
hydroborating alkenes at room temperature. An unusual hydroboration
mechanism is discussed. Hydroboration of alkynes with Py·BH2I
selectively affords the monoadducts. The preparation of synthetically useful
potassium alkyltrifluoroborate salts is described.
J. M. Clay, E. Vedejs, J. Am. Chem. Soc.,
2005, 127, 5766-5767.
Sodium perborate: a mild and convenient reagent for efficiently oxidizing
organoboranes
G. W. Kabalka, T. M. Shoup, N. M. Goudgaon, J. Org. Chem., 1989, 5930-5933.
A mild, atom-economical, Au(III)-catalyzed hydration of 3-alkynoates allows a
practical one-step synthesis of a wide range of γ-keto esters in good yields,
through a carbonyl group participation enabled by a favored 5-endo-dig
cyclization.
W. Wang, B. Xu, G. B. Hammond, J. Org. Chem., 2009,
74, 1640-1643.
An efficient, indirect anti-Markovnikov hydration of unsymmetrically substituted
terminal and internal alkynes is based on TiCl4-catalyzed
hydroamination reactions. Its application to ortho-alkynylhaloarenes,
followed by a copper-catalyzed O-arylation, provides substituted
benzo[b]furans.
L. Ackermann, L. T. Kaspar, J. Org. Chem., 2007,
72, 6149-6153.
A ruthenium-catalyzed hydrative cyclization converts a range of 1,5-enynes
bearing terminal alkyne and Michael acceptor moieties into cyclopentanone
derivatives.
Y. Chen, D. M. Ho, C. Lee, J. Am. Chem. Soc.,
2005, 127, 12184-12185.
