Categories: C-C Bond Formation > Arenes >
Synthesis of aryl ketones
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Stable and non-hygroscopic aluminum
dodecatungstophosphate (AlPW12O40), which is prepared
easily from cheap and commercially available compounds, is an
effective catalyst for Friedel-Crafts acylation reactions using carboxylic
acids, acetic anhydride and benzoyl chloride in the absence of solvent under
mild reaction conditions.
H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Tetrahedron, 2004,
60, 10843-10850.
The palladium acetate-catalyzed coupling reaction of aryl boronic acids with
carboxylic anhydrides or acyl chlorides was carried out smoothly in water in
the presence of PEG or [bmim][PF6] to give high yields of
ketones. The Pd(OAc)2-H2O-[bmim][PF6]
catalytic system can be recovered and reused.
B. Xin, Yuhong Zhang, K. Cheng, J. Org. Chem., 2006,
71, 5725-5731.
A palladium(II) chloride catalyzed mild cross-coupling of arylboronic acids with
carboxylic anhydrides or acyl chlorides in water in the presence of the
inexpensive surfactant sodium dodecyl sulfate (SDS) gives aryl ketones in good
yields without the use of phosphine ligands.
B. Xin, Y. Zhang, K. Cheng, Synthesis, 2007,
1970-1978.
A direct cross-coupling reaction of aromatic aldehydes with potassium
trifluoro(organo)borates afforded ketones in high yields and under mild
conditions in the presence of a rhodium catalyst and acetone.
M. Pucheault, S. Darses, J-P. Genet, J. Am. Chem. Soc.,
2004,
126, 15356-15357.
A new palladium-catalyzed cross-coupling reaction between arylboronic
acids and mixed anhydrides, generated in situ from carboxylic acids and
pivalic anhydride, is presented.
L. J. Goossen, K. Ghosh, Eur. J. Org. Chem., 2002,
3254-3267.
A new Ni catalyst is capable of effecting the rapid cross-coupling of acid
fluorides, acid chlorides, acyl cyanides, anhydrides, thioesters, and
pyridyl esters with both groups of diorganozinc reagents. Reactions with
acid fluorides as electrophilic partners tolerate epimerizable functionality
as well as leaving groups.
Y. Zhang, T. Rovis, J. Am. Chem. Soc.,
2004,
126, 15964-15965.
Palladium-catalyzed couplings of aryl bromides with N-tert-butylhydrazones as
acyl anion equivalents
occurs at the C-position to form N-tert-butyl azo compounds.
Isomerization of these azo compounds to the corresponding hydrazones, followed
by hydrolysis, gave the desired mixed alkyl aryl ketones.
A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc., 2006,
128, 14800-14801.
The use of Zn powder in the presence of LiCl in THF allows a simple,
high-yielding preparation of a broad range of functionalized aryl- and
heteroarylzinc reagents. The synthesis of alkylzinc reagents was performed
from inexpensive alkyl bromides.
A. Krasovski, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. Int. Ed., 2006,
45, 6040-6044.
Chemoselective cross-coupling of aliphatic and aromatic acyl chlorides with
organostannanes provides a useful alternative to Friedel-Crafts acylations
for the synthesis of ketones. A range of ketones are obtained in high yield
using 2.5 mol % of bis(di-tert-butylchlorophosphine)palladium(II)
dichloride as precatalyst. The catalyst tolerates various functional groups
including aryl chlorides and bromides that usually undergo oxidative
addition to palladium complexes.
R. Lerebours, A. Camacho-Soto, C. Wolf, J. Org. Chem., 2005,
70, 8601-8604.
The palladium-catalyzed coupling of 2-pyridyl
esters with organoboron compounds is compatible with various functional groups
and proceeds under mild reaction conditions. The coordination of the nitrogen
atom to Pd is a key step for an efficient reaction.
H. Tatamidani, F. Kakiuchi, N. Chatani, Org. Lett., 2004, 6,
3597-3599.
meso-2,4-Bis(diphenylphosphino)pentane (mBDPP) is an effective
regiocontrolling ligand for palladium-catalyzed internal arylation of
electron-rich olefins in DMSO with no need for any halide scavengers.
S. Liu, N. Berry, N. Thomson, A. Pettman, Z. Hyder, J. Mo, J. Xiao, J. Org. Chem., 2006,
71, 7467-7470.
Ammonium salts that can act as hydrogen-bond donors exert a remarkable
acceleration on the rates of the regioselective arylation of electron-rich
olefins by aryl halides in ionic liquids and common solvents.
J. Mo, J. Xiao, Angew. Chem. Int. Ed., 2006,
45, 4152-4157.
Palladium-catalyzed regioselective Heck arylation of various electron-rich
olefins has been accomplished in imidazolium ionic liquids with a wide range
of aryl bromides and iodides. The reaction proceeded with high efficiency
and remarkable regioselectivity. The chemistry provides a simple, effective
method for preparing branched olefins and contributes to the extension of
the Heck reaction to a wider range of substrates.
J. Mo, L. Xu, J. Xiao, J. Am. Chem. Soc.,
2005,
127, 751-760.
Silylated cyanohydrins of iodo-substituted aryl, heteroaryl, or cycloalkenyl
ketones undergo an I/Mg-exchange using i-PrMgCl·LiCl. After
subsequent reactions with electrophiles, a facile deprotection
produces polyfunctional ketones in good overall yiels. An extension to
aromatic iodoaldehydes is described.
C.-Y. Liu, H. Ren, P. Knochel, Org. Lett.,
2006,
8, 617-629.
Highly regioselective and efficient Heck reactions of aryl triflates with
N-acyl-N-vinylamines were achieved using 1.5 mol-% of Pd2(dba)3,
3 mol-% of dppf, and diethylisopropylamine in dioxane. The Heck coupling
products easily underwent acidic hydrolysis to the corresponding aryl methyl
ketones.
A. L. Hansen, T. Skydstrup, J. Org. Chem., 2005,
70, 5997-6003.
A new method for the synthesis of organoborates starting from
α,β-unsaturated acetals was developed. The available alkoxy-functionalized
butadienyl- and styrylboronic esters cross couple effectively with a broad
spectrum of aryl halides under mild conditions. The new methods also provide
an effective approach to aromatic ketones.
P. B. Tivola, A. Deagostino, C. Prandi, P. Venturello, Org. Lett.,
2002, 4, 1275-1277.
1-Siloxy-1-alkenylcopper species were generated by 1,2-Csp2-to-O
silyl migration of the copper enolates of acyltriphenylsilanes. The
alkenylcopper species reacted with methyl, benzyl, allylic, tributylstannyl
halides and in the presence of Pd(0) catalyst with aryl and alkenyl iodides
to give geometrically pure (Z)-enol silyl ethers.
A. Tsubouchi, K. Onishi, T. Takeda, J. Am. Chem. Soc., 2006,
128, 14268-14269.
The first enantioselective desymmetrizations of anhydrides with carbon-based
nucleophiles nucleophiles by employing (-)-sparteine as a chiral ligand are
described. These C-C bond-forming reactions proceed in good enantioselectivity
for a range of anhydrides.
R. Shintani, G. C. Fu, Angew. Chem. Int. Ed., 2002, 41,
1057-1059.
Tetraorganoindates, which are easily prepared from 1 eq. of InCl3
and 4 eq. of organometallics, could be employed as effective nucleophilic
cross-coupling partners in Pd-catalyzed carbonylative cross-coupling
reactions with a variety of halides. The present method gave unsymmetrical
ketones in good yields.
S. W. Lee, K. Lee, D. Seomoon, S. Kim, H. Kim, H. Kim, E. Shim, M. Lee,
J. Org. Chem., 2004, 69, 4852-4855.
The use of titanium(IV) chloride as a Lewis acid for direct ortho-acylation
of phenols and naphthols proves to be a convenient, more general and direct
route to various hydroxyaryl ketones. The route is regioselective, leading
to ortho C-acylated products in satisfactory to high yields in most cases.
A. Bensari, N. T. Zaveri, Synthesis,
2003, 267-271
A Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction at
room temperature was achieved by using water as a solvent under balloon
pressure of CO with Et3N as a base.
B. Liang, M. Huang, Z. You, Z. Xiong, K. Lu, R. Fathi, J. Chen, Z. Yang,
J. Org. Chem., 2005,
70, 6097-6100.
Carbonylative coupling of terminal alkynes with aryliodides in the
presence of PdCl2(PPh3)2 as catalyst in 2
eq. of 0.5 M aqueous ammonia, and CO (1 atm) gives the corresponding
α,β-alkynyl ketones in good yields.
M. S. M. Ahmed, A. Mori, Org. Lett., 2003, 5,
3057-3060.
The Pd-catalyzed reaction between aryl or vinyl iodides and ethyl diazoacetate
(EDA) provides cross-coupling products in good yields.
C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc., 2007,
129, 8708-8709.
Indanones and 2-cyclopentenones have been successfully prepared in good to
excellent yields by the palladium-catalyzed carbonylative cyclization of
unsaturated aryl iodides and dienyl triflates, iodides, and bromides,
respectively. The mechanism is discussed.
S. V. Gagnier, R. C. Larock, J. Am. Chem. Soc., 2003,
125, 4804-4807.
Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and
alkenes afforded substituted tetralone and cyclohexenone derivatives. A wide
range of substrates can be employed in these carbocyclizations.
L. Zhang, S. A. Kozmin, J. Am. Chem. Soc.,
2004,
126, 10204-10205.
