Categories: C-C Bond Formation > Arenes >
Synthesis of aryl ketones
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Recent Literature
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 direct acylation of aryl bromides with aldehydes involves palladium-amine
cooperative catalysis, affording synthetically important alkyl aryl ketones in
good yields in a straightforward manner, and broadening the scope of
metal-catalyzed coupling reactions.
J. Ruan, O. Saidi, J. A. Iggo, J. Xiao, J. Am. Chem. Soc., 2008,
130, 10510-10511.
A convenient and efficient method allows the synthesis of various arylketones by
nickel-catalyzed addition of arylboronic acids to nitriles. A catalytic cycle
involving Ni(II) species as the catalytic intermediates is proposed.
Y.-C. Wong, K. Parthasarathy, C.-H. Cheng, Org. Lett., 2010,
12, 1736-1739.
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.
An addition of arylboronic acids to nitriles catalyzed by a
bipyridine-cyclopalladated ferrocenylimine complex can be conducted in aqueous
media under acidic or basic conditions. The addition of NH4Cl has a
drastic effect on the reaction yields.
A. Yu, J. Li, M. Cui, Y. Wu, Synlett, 2007, 3063-3067.
A mild and general protocol for the carbonylative Suzuki-Miyaura cross-coupling
of sterically hindered ortho-disubstituted aryl iodides with various aryl
boronic acids provides an array of substituted biaryl ketones in good yield. A
carbonylative Negishi coupling that utilizes alkynyl nucleophiles is also
described.
B. M. O'Keefe, N. Simmons, S. F. Martin, Org. Lett.,
2008,
10, 5301-5304.
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.
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.
A mild and efficient protocol for palladium-catalyzed oxidative Heck reactions
of arylboronic acids with both electron-rich and -deficient olefins works in the
absence of a base, oxygen, or other external oxidants. With a wide variety of
substrates tolerated, the method broadens the scope of palladium-catalyzed
coupling reactions.
J. Ruan, X. Li, O. Saidi, J. Xiao, J. Am. Chem. Soc., 2008,
130, 2424-2425.
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 Pd2(dba)3, dppf, and diethylisopropylamine in dioxane. The coupling products easily
underwent acidic hydrolysis to the corresponding aryl methyl ketones or in situ
hydrogenation in the presence of (Ph3P)3RhCl under a
hydrogen atmosphere to provide the N-acyl derivatives of benzylic amines.
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.
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 new, anionic four-electron donor-based (type I) palladacycle-catalyzed
sequential reaction of 2-bromobenzaldehydes with arylboronic acids based on the
addition reaction, cyclization via C-H activation-oxidation sequence provides an efficient access to a variety of substituted
fluorenones/indenofluorenediones from readily available starting materials.
T.-P. Liu, Y.-X. Liao, C.-H. Xing, Q.-S. Hu, Org. Lett., 2011,
13, 2452-2455.
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.
