General and mild Ni(0)-catalyzed α-arylation of ketones using aryl chlorides.

A general methodology for the α-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin)Cl] (1 c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni-N-heterocyclic carbene (NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni(0)/Ni(II) catalytic cycle to be at play.

[1]  Yu Liu,et al.  Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2. , 2014, Journal of the American Chemical Society.

[2]  T. Jamison,et al.  Highly regioselective nickel-catalyzed cross-coupling of N-tosylaziridines and alkylzinc reagents. , 2014, Journal of the American Chemical Society.

[3]  A. Slawin,et al.  Nickel-catalysed carboxylation of organoboronates. , 2014, Chemical communications.

[4]  Junichiro Yamaguchi,et al.  Nickel-catalyzed α-arylation of ketones with phenol derivatives. , 2014, Angewandte Chemie.

[5]  S. Minakata,et al.  Pd/NHC-catalyzed enantiospecific and regioselective Suzuki-Miyaura arylation of 2-arylaziridines: synthesis of enantioenriched 2-arylphenethylamine derivatives. , 2014, Journal of the American Chemical Society.

[6]  D. J. Nelson,et al.  Efficient C-N and C-S bond formation using the highly active [Ni(allyl)Cl(IPr*OMe)] precatalyst , 2014 .

[7]  T. Jamison,et al.  Recent advances in homogeneous nickel catalysis , 2014, Nature.

[8]  Mickaël Henrion,et al.  From acetone metalation to the catalytic α-arylation of acyclic ketones with NHC-nickel(II) complexes. , 2014, Chemical communications.

[9]  N. Chatani,et al.  Nickel-catalyzed reductive and borylative cleavage of aromatic carbon-nitrogen bonds in N-aryl amides and carbamates. , 2014, Journal of the American Chemical Society.

[10]  T. Jamison,et al.  A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes , 2014, Organometallics.

[11]  M. Ohashi,et al.  One-Pot, Single-Step, and Gram-Scale Synthesis of Mononuclear [(η6-arene)Ni(N-heterocyclic carbene)] Complexes: Useful Precursors of the Ni0–NHC Unit , 2014 .

[12]  T. Jamison,et al.  Nickel-catalyzed Mizoroki-Heck reaction of aryl sulfonates and chlorides with electronically unbiased terminal olefins: high selectivity for branched products. , 2014, Angewandte Chemie.

[13]  P. Walsh,et al.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides. , 2014, Advanced synthesis & catalysis.

[14]  Yixiang Cheng,et al.  Synthesis of functionalized isoquinolin-1(2H)-ones by copper-catalyzed α-arylation of ketones with 2-halobenzamides. , 2013, Chemistry.

[15]  J. Hartwig,et al.  Palladium-catalyzed α-arylation of zinc enolates of esters: reaction conditions and substrate scope. , 2013, The Journal of organic chemistry.

[16]  P. Walsh,et al.  Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides. , 2013, Organic letters.

[17]  M. Stradiotto,et al.  Addressing challenges in palladium-catalyzed cross-couplings of aryl mesylates: monoarylation of ketones and primary alkyl amines. , 2013, Angewandte Chemie.

[18]  J. Hartwig,et al.  Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides. , 2012, Angewandte Chemie.

[19]  M. Taillefer,et al.  Direct copper-catalyzed α-arylation of benzyl phenyl ketones with aryl iodides: route towards tamoxifen. , 2012, Angewandte Chemie.

[20]  M. Stradiotto,et al.  Palladium‐Catalyzed Mono‐α‐arylation of Carbonyl‐Containing Compounds with Aryl Halides using DalPhos Ligands , 2012 .

[21]  M. Iglesias,et al.  Kumada-Tamao-Corriu coupling of heteroaromatic chlorides and aryl ethers catalyzed by (IPr)Ni(allyl)Cl. , 2012, Organic letters.

[22]  L. Ackermann,et al.  Palladium-catalyzed mono-α-arylation of acetone with aryl imidazolylsulfonates. , 2012, Chemistry.

[23]  J. Hartwig,et al.  Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions. , 2011, Journal of the American Chemical Society.

[24]  Petr Martin Pd-catalyzed α-Arylation of Carbonyl and Related Compounds: Recent Developments and Perspectives , 2011 .

[25]  M. Stradiotto,et al.  Palladium-catalyzed mono-α-arylation of acetone with aryl halides and tosylates. , 2011, Journal of the American Chemical Society.

[26]  M. Iglesias,et al.  Well-Defined Allylnickel Chloride/N-Heterocyclic Carbene [(NHC)Ni(allyl)Cl] Complexes as Highly Active Precatalysts for CN and CS Cross-Coupling Reactions , 2010 .

[27]  R. Rossi,et al.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides. , 2010, Chemical reviews.

[28]  Thomas J. Colacot,et al.  Metal-catalyzed alpha-arylation of carbonyl and related molecules: novel trends in C-C bond formation by C-H bond functionalization. , 2010, Angewandte Chemie.

[29]  Thomas J. Colacot,et al.  Metallkatalysierte α‐Arylierungen von Carbonylen und verwandten Molekülen: aktuelle Trends bei der C‐C‐Kupplung über C‐H‐Funktionalisierung , 2010 .

[30]  X. Bai,et al.  Multiwall boron carbonitride/carbon nanotube junction and its rectification behavior. , 2007, Journal of the American Chemical Society.

[31]  K. Hara,et al.  Nickel-NHC-catalyzed alpha-arylation of acyclic ketones and amination of haloarenes and unexpected preferential N-arylation of 4-aminopropiophenone. , 2007, The Journal of organic chemistry.

[32]  A. Chan,et al.  Nickel-catalyzed asymmetric α-arylation of ketone enolates , 2006 .

[33]  Jianguo Mei,et al.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. , 2006, Journal of the American Chemical Society.

[34]  J. Hartwig,et al.  Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles , 2003 .

[35]  S. Buchwald,et al.  Nickel-BINAP Catalyzed Enantioselective a-Arylation of a-Substituted ?-Butyrolactones , 2002 .

[36]  J. Snyder,et al.  Total synthesis of SR 121463 A, a highly potent and selective vasopressin v(2) receptor antagonist. , 2001, The Journal of organic chemistry.

[37]  J. Hartwig,et al.  Palladium-Catalyzed Direct α-Arylation of Ketones. Rate Acceleration by Sterically Hindered Chelating Ligands and Reductive Elimination from a Transition Metal Enolate Complex , 1997 .

[38]  S. Buchwald,et al.  Palladium-Catalyzed α-Arylation of Ketones , 1997 .

[39]  T. Satoh,et al.  Palladium‐Catalyzed Regioselective Mono‐ and Diarylation Reactions of 2‐Phenylphenols and Naphthols with Aryl Halides , 1997 .

[40]  M. Miura,et al.  Palladiumkatalysierte regioselektive Monound Diarylierung von 2‐Phenylphenolen und Naphtholen mit Arylhalogeniden , 1997 .

[41]  W. B. Wright,et al.  Thromboxane synthetase inhibitors and antihypertensive agents. 1. N-[(1H-imidazol-1-yl)alkyl]aryl amides and N-[(1H-1,2,4-triazol-1-yl)alkyl]aryl amides. , 1986, Journal of medicinal chemistry.

[42]  J. F. Wolfe,et al.  Photoinduced cyclizations of mono- and dianions of N-acyl-o-chloroanilines and N-acyl-o-chlorobenzylamines as general methods for the synthesis of oxindoles and 1,4-dihydro-3(2H)-isoquinolinones , 1985 .