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 catalyst comprising of Ph3PAuCl and AgSbF6 efficiently
hydrolyzes terminal alkyne groups of propargyl acetates in the absence of acid
promoters at ambient temperature within a short time. Effective regioselective
hydration is facilitated by the neighboring carbonyl group. Synthesis of
actinopolymorphol B is achieved involving hydration of the propargyl acetate as
the key step.
N. Ghosh, S. Nayak, A. K. Sahoo, J. Org. Chem., 2011,
76, 500-511.
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.
An expedient and reliable method for accessing reactive α-oxo gold carbenes via
gold-catalyzed intermolecular oxidation of terminal alkynes offers a safe and
economical alternative to strategies based on diazo substrates. Its synthetic
potential is demonstrated by expedient preparation of dihydrofuran-3-ones
containing a broad range of functional groups.
L. Ye, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc., 2010,
132, 3258-3259.
Related
A rhodium-catalyzed, selective intermolecular anti-Markovnikov addition
of carboxylic acids to terminal alkynes gives valuable Z-enol esters. The
catalyst system is applicable to a broad substrate scope and displays a wide
functional group tolerance.
A. Lumbroso, N. R. Vautravers, B. Breit, Org. Lett., 2010,
12, 5498-5501.
PPh3AuCl/AgPF6-catalyzed hydroacyloxylation of alkynes
with carboxylic acids affords the Markonikov addition products, whereas PPh3AuCl/AgOTf
catalyst gives the more stable isomerized products via the Markonikov products.
B. C. Chary, S. Kim, J. Org. Chem., 2010,
75, 7928-7931.
