Nickel-catalyzed direct C-H/C-O cross couplings generating fluorobenzenes and heteroarenes.

The Ni-catalyzed direct C-H/C-O cross couplings of benzylic alcohol derivatives with fluorobenzenes and heteroarenes are disclosed. This transformation provides a straightforward and efficient method for the synthesis of these valuable heteroatom-containing compounds.

[1]  Rúben Martín,et al.  Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity. , 2014, Chemical Society reviews.

[2]  E. R. Jarvo,et al.  Stereospecific Cross-Coupling Reactions of Aryl-Substituted Tetrahydrofurans, Tetrahydropyrans, and Lactones , 2014, Journal of the American Chemical Society.

[3]  G. Panda,et al.  Synthetic methodologies of achiral diarylmethanols, diaryl and triarylmethanes (TRAMs) and medicinal properties of diaryl and triarylmethanes-an overview , 2014 .

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

[5]  K. Hirano,et al.  Synthesis of triarylmethanes by palladium-catalyzed C-H/C-O coupling of oxazoles and diarylmethanol derivatives. , 2014, The Journal of organic chemistry.

[6]  Haizhu Yu,et al.  Mechanistic study of chemoselectivity in Ni-catalyzed coupling reactions between azoles and aryl carboxylates. , 2014, Journal of the American Chemical Society.

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

[8]  Rúben Martín,et al.  A mild Ni/Cu-catalyzed silylation via C-O cleavage. , 2014, Journal of the American Chemical Society.

[9]  Ruben Martin,et al.  Ni-catalyzed carboxylation of C(sp2)- and C(sp3)-O bonds with CO2. , 2014, Journal of the American Chemical Society.

[10]  E. R. Jarvo,et al.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters. , 2013, Journal of the American Chemical Society.

[11]  Jianmei Lu,et al.  N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed Suzuki-Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water. , 2013, Organic & biomolecular chemistry.

[12]  C. Moore,et al.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst. , 2013, Journal of the American Chemical Society.

[13]  S. Gong,et al.  Convenient Deoxygenation of Aromatic Ketones by Silica-Supported Chitosan Schiff Base Palladium Catalyst , 2012 .

[14]  Junichiro Yamaguchi,et al.  Nickel-catalyzed C-H/C-O coupling of azoles with phenol derivatives. , 2012, Journal of the American Chemical Society.

[15]  Amitabha Sarkar,et al.  Palladium nanoparticle catalysis: borylation of aryl and benzyl halides and one-pot biaryl synthesis via sequential borylation-Suzuki–Miyaura coupling , 2012 .

[16]  Lok Nath Neupane,et al.  Tris(pentafluorophenyl)borane [B(C6F5)3]-catalyzed Friedel–Crafts reactions of activated arenes and heteroarenes with α-amidosulfones: the synthesis of unsymmetrical triarylmethanes , 2011 .

[17]  J. Canivet,et al.  Nickel-catalyzed C-H arylation of azoles with haloarenes: scope, mechanism, and applications to the synthesis of bioactive molecules. , 2011, Chemistry.

[18]  Daniel R. Zuidema,et al.  Deoxygenation of Aromatic Ketones Using Transfer Hydrogenolysis with Raney Nickel in 2-Propanol , 2011 .

[19]  V. Percec,et al.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds. , 2011, Chemical reviews.

[20]  Da‐Gang Yu,et al.  Exploration of new C-O electrophiles in cross-coupling reactions. , 2010, Accounts of chemical research.

[21]  S. Soo Kim,et al.  Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes catalyzed by FeCl3 x 6 H2O: synthesis of triarylmethanes and bis-heteroarylarylmethanes. , 2010, The Journal of organic chemistry.

[22]  L. Ackermann Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides. , 2010, Chemical communications.

[23]  T. Jamison,et al.  Nickel-catalyzed allylic substitution of simple alkenes. , 2010, Journal of the American Chemical Society.

[24]  Amitabha Sarkar,et al.  Palladium nanoparticle catalyzed Hiyama coupling reaction of benzyl halides. , 2010, The Journal of organic chemistry.

[25]  T. Sivakumar,et al.  Room temperature efficacious synthesis of diphenylmethane over Fe/Al-MCM-41 catalysts , 2010 .

[26]  K. Hirano,et al.  Palladium-catalyzed direct benzylation of azoles with benzyl carbonates. , 2010, Organic letters.

[27]  B. Lipshutz,et al.  Cross-couplings between benzylic and aryl halides "on water": synthesis of diarylmethanes. , 2010, Chemical communications.

[28]  G. Olah,et al.  BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives. , 2009, The Journal of organic chemistry.

[29]  R. SanMartin,et al.  Insights into the Role of New Palladium Pincer Complexes as Robust and Recyclable Precatalysts for Suzuki–Miyaura Couplings in Neat Water , 2009 .

[30]  H. Amii,et al.  C-F bond activation in organic synthesis. , 2009, Chemical reviews.

[31]  M. Wilkinson,et al.  Iron-catalysed Negishi coupling of benzyl halides and phosphates. , 2009, Chemical communications.

[32]  R. SanMartin,et al.  A nonsymmetric pincer-catalyzed Suzuki-Miyaura arylation of benzyl halides and other nonactivated unusual coupling partners. , 2008, The Journal of organic chemistry.

[33]  P. Knochel,et al.  Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates. , 2008, Chemical communications.

[34]  A. Vinu,et al.  Highly active three-dimensional cage type mesoporous ferrosilicate catalysts for the Friedel–Crafts alkylation , 2008 .

[35]  P. Knochel,et al.  LiCl-mediated preparation of highly functionalized benzylic zinc chlorides. , 2008, Organic letters.

[36]  J. Yu,et al.  Suzuki-Miyaura coupling of diarylmethyl carbonates with arylboronic acids: a new access to triarylmethanes. , 2008, Organic letters.

[37]  S. Purser,et al.  Fluorine in medicinal chemistry. , 2008, Chemical Society reviews.

[38]  C. Bruneau,et al.  Activation and functionalization of benzylic derivatives by palladium catalysts. , 2008, Chemical Society reviews.

[39]  A. L. Monteiro,et al.  Synthesis of diarylmethane derivatives from Stille cross-coupling reactions of benzylic halides , 2007 .

[40]  F. Diederich,et al.  Fluorine in Pharmaceuticals: Looking Beyond Intuition , 2007, Science.

[41]  Duong Tuan Quang,et al.  Calixarene-derived fluorescent probes. , 2007, Chemical reviews.

[42]  P. Knochel,et al.  Synthesis of functionalized diarylmethanes via a copper-catalyzed cross-coupling of arylmagnesium reagents with benzylic phosphates. , 2006, Organic letters.

[43]  V. Nair,et al.  Recent Advances in the Chemistry of Triaryl- and Triheteroarylmethanes , 2006 .

[44]  K. Laali,et al.  Facile benzylation of aromatics in ionic liquid solvents promoted by TfOH, Sc(OTf)3, and Yb(OTf)3·xH2O; New life for a classic transformation , 2006 .

[45]  G. Olah,et al.  BF3.2CF3CH2OH (BF3.2TFE), an efficient superacidic catalyst for some organic synthetic transformations. , 2006, The Journal of organic chemistry.

[46]  J. Esquivias,et al.  A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines: synthesis of unsymmetrical diaryl amines and triaryl methanes. , 2006, Angewandte Chemie.

[47]  B. Bandgar,et al.  Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions , 2004 .

[48]  R. Shoemaker,et al.  Rational design and synthesis of novel dimeric diketoacid-containing inhibitors of HIV-1 integrase: implication for binding to two metal ions on the active site of integrase. , 2004, Journal of medicinal chemistry.

[49]  F. Diederich,et al.  Interactions with aromatic rings in chemical and biological recognition. , 2003, Angewandte Chemie.

[50]  G. Olah,et al.  Reduction of carbonyl groups to the corresponding methylenes with Ni-Al alloy in water. , 2003, Chemical communications.

[51]  K. Rice,et al.  Development of long-acting dopamine transporter ligands as potential cocaine-abuse therapeutic agents: chiral hydroxyl-containing derivatives of 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine and 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine. , 2002, Journal of medicinal chemistry.

[52]  P. Knochel,et al.  Copper-mediated cross-coupling of functionalized arylmagnesium reagents with functionalized alkyl and benzylic halides. , 2001, Organic letters.

[53]  J. Sherman,et al.  Carceplexes and Hemicarceplexes. , 1999, Chemical reviews.

[54]  J. Rebek,et al.  Self-Assembling Capsules. , 1997, Chemical reviews.

[55]  P. Knochel,et al.  New multi-coupling benzylic zinc reagents for the preparation of flexible aromatic compounds , 1997 .

[56]  Junichiro Yamaguchi,et al.  Recent Progress in Nickel‐Catalyzed Biaryl Coupling , 2013 .

[57]  N. Chatani,et al.  Catalytic Transformations Involving the Activation of sp 2 Carbon–Oxygen Bonds , 2012 .

[58]  J. Dutasta,et al.  Cryptophanes and their complexes--present and future. , 2009, Chemical reviews.

[59]  M. Irving,et al.  Electrophilic aromatic substitution. 12. Kinetic studies of the titanium tetrachloride-catalyzed reactions of benzyl chloride, p-xylyl chloride, and p-nitrobenzyl chloride with benzene and anisole in nitromethane and dichloromethane , 1990 .