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Synthesis of aryl ketones

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Friedel-Crafts Acylation


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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 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.