Direct C-2 Alkylation of Quinoline N-Oxides with Ethers via Palladium-Catalyzed Dehydrogenative Cross-Coupling Reaction

An efficient and concise one-pot strategy for the direct alkylation of quinoline N-oxides via palladium-catalyzed dual CH bonds activation has been developed. This methodology provides quinoline-containing heterocyclic molecules in moderate to excellent yields.

[1]  X. Chen,et al.  Palladium(II)‐katalysierte C‐H‐Aktivierung/C‐C‐Kreuzkupplung: Vielseitigkeit und Anwendbarkeit , 2009 .

[2]  Chao‐Jun Li,et al.  FeCl2-catalyzed selective C--C bond formation by oxidative activation of a benzylic C--H bond. , 2007, Angewandte Chemie.

[3]  jin-quan yu,et al.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. , 2009, Angewandte Chemie.

[4]  Melanie S Sanford,et al.  Palladium-catalyzed ligand-directed C-H functionalization reactions. , 2010, Chemical reviews.

[5]  T. Mei,et al.  Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. , 2012, Accounts of chemical research.

[6]  L. Palmisano,et al.  Sunlight-induced reactions of some heterocyclic bases with ethers in the presence of TiO2: A green route for the synthesis of heterocyclic aldehydes , 2005 .

[7]  J. Yoshida,et al.  Metal- and chemical-oxidant-free C-H/C-H cross-coupling of aromatic compounds: the use of radical-cation pools. , 2012, Angewandte Chemie.

[8]  J. Muzart,et al.  Intermolecular dehydrogenative Heck reactions. , 2011, Chemical reviews.

[9]  P. Mayer,et al.  Palladium‐katalysierte dehydrierende Kreuzkupplungen von Benzazolen mit Azolen , 2011 .

[10]  H. Reichenbach,et al.  The aurachins, new quinoline antibiotics from myxobacteria: production, physico-chemical and biological properties. , 1987, The Journal of antibiotics.

[11]  F. Meng,et al.  14-Aminocamptothecins: their synthesis, preclinical activity, and potential use for cancer treatment. , 2011, Journal of medicinal chemistry.

[12]  Chao‐Jun Li Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations. , 2009, Accounts of chemical research.

[13]  Chao‐Jun Li,et al.  CuBr-catalyzed efficient alkynylation of sp3 C-H bonds adjacent to a nitrogen atom. , 2004, Journal of the American Chemical Society.

[14]  Jun Lu,et al.  Calothrixins, a new class of human DNA topoisomerase I poisons. , 2009, Journal of natural products.

[15]  H. W. Lam,et al.  Functionalization of Csp3-H and Csp2-H bonds: synthesis of spiroindenes by enolate-directed ruthenium-catalyzed oxidative annulation of alkynes with 2-aryl-1,3-dicarbonyl compounds. , 2012, Angewandte Chemie.

[16]  Chao‐Jun Li,et al.  Highly efficient copper-catalyzed nitro-Mannich type reaction: cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond. , 2005, Journal of the American Chemical Society.

[17]  X. Wan,et al.  Bu4NI-catalyzed C-O bond formation by using a cross-dehydrogenative coupling (CDC) reaction. , 2011, Chemistry.

[18]  M. Litaudon,et al.  Antiplasmodial alkaloids from Desmos rostrata. , 2008, Journal of natural products.

[19]  Chang-Liang Sun,et al.  Direct C-H transformation via iron catalysis. , 2011, Chemical reviews.

[20]  G. Höfle,et al.  Isolation and biosynthesis of aurachin P and 5-nitroresorcinol from Stigmatella erecta. , 2008, Journal of natural products.

[21]  C. Kappe,et al.  Copper-catalyzed formation of C-O bonds by direct α-C-H bond activation of ethers using stoichiometric amounts of peroxide in batch and continuous-flow formats. , 2012, Chemistry.

[22]  C. Bruneau,et al.  Ruthenium(II)-catalyzed C-H bond activation and functionalization. , 2012, Chemical reviews.

[23]  Lei Wang,et al.  Palladium-catalyzed ortho-acylation of acetanilides with aldehydes through direct C-H bond activation. , 2011, Chemistry.

[24]  Chao‐Jun Li,et al.  CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds. , 2005, Journal of the American Chemical Society.

[25]  F. Fontana,et al.  Polar effects in free-radical reactions. Rate constants in phenylation and new methods of selective alkylation of heteroaromatic bases. , 1986 .

[26]  R. Mahieux,et al.  Substituted quinolines induce inhibition of proliferation of HTLV-1 infected cells. , 2003, Bioorganic & medicinal chemistry letters.

[27]  C. Yeung,et al.  Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds. , 2011, Chemical reviews.

[28]  Zhangjie Shi,et al.  Introduction: CH Activation. , 2017, Chemical reviews.

[29]  Chao‐Jun Li,et al.  Sc(OTf)3-catalyzed direct alkylation of quinolines and pyridines with alkanes. , 2009, Organic letters.

[30]  K. Möller,et al.  Organoboron Quinolinolates with Extended Conjugated Chromophores: Synthesis, Structure, and Electronic and Electroluminescent Properties , 2006 .

[31]  Chao‐Jun Li,et al.  Palladium-catalyzed oxidative sp2 C-H bond acylation with alcohols. , 2011, Organic letters.

[32]  P. Mayer,et al.  Palladium-catalyzed dehydrogenative cross-couplings of benzazoles with azoles. , 2011, Angewandte Chemie.

[33]  H. Mankin,et al.  Synthesis and evaluation of (2-(4-methoxyphenyl)-4-quinolinyl)(2-piperidinyl)methanol (NSC23925) isomers to reverse multidrug resistance in cancer. , 2012, Journal of medicinal chemistry.

[34]  Chao‐Jun Li,et al.  Highly efficient direct alkylation of activated methylene by cycloalkanes , 2007 .

[35]  F. Minisci,et al.  Polar effects in free-radical reactions. New synthetic developments in the functionalization of heteroaromatic bases by nucleophilic radicals , 1985 .

[36]  Zhangjie Shi,et al.  From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation. , 2012, Chemical Society reviews.

[37]  F. Minisci,et al.  Redox-chain decomposition of hydroxylamine-O-sulphonic acid. A novel general source of nucleophilic radicals for the functionalization of heteroaromatic bases , 1983 .

[38]  F. Fontana,et al.  Polar effects in free-radical reactions. Selectivity and reversibility in the homolytic benzylation of protonated heteroaromatic bases , 1986 .

[39]  Siegfried R. Waldvogel,et al.  Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol. , 2012, Journal of the American Chemical Society.

[40]  Lei Wang,et al.  Direct C2-alkylation of azoles with alcohols and ethers through dehydrogenative cross-coupling under metal-free conditions. , 2011, Organic letters.

[41]  Chao‐Jun Li,et al.  Ruthenium-catalyzed para-selective oxidative cross-coupling of arenes and cycloalkanes. , 2011, Organic letters.

[42]  F. Minisci,et al.  Polar effects in free radical reactions. Induced decompositions of peroxo compounds in the substitution of heteroaromatic bases by nucleophilic radicals , 1984 .

[43]  Chao‐Jun Li,et al.  Palladium-catalyzed Minisci reaction with simple alcohols. , 2011, Organic letters.

[44]  P. Pihko,et al.  Palladium-catalyzed dehydrogenative β'-functionalization of β-keto esters with indoles at room temperature. , 2012, Journal of the American Chemical Society.

[45]  V. Avery,et al.  Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras. , 2009, Journal of natural products.

[46]  B. Jankiewicz,et al.  Reactivity of the 4,5-didehydroisoquinolinium cation. , 2012, Chemistry.

[47]  Haijun Li,et al.  Iron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms. , 2008, Angewandte Chemie.

[48]  Johannes E. M. N. Klein,et al.  Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates. , 2009, Journal of the American Chemical Society.

[49]  B. Kunze,et al.  Biosynthesis of aurachins A-L in Stigmatella aurantiaca: a feeding study. , 2008, Journal of natural products.

[50]  M. Sanford,et al.  Controlling site selectivity in Pd-catalyzed oxidative cross-coupling reactions. , 2011, Journal of the American Chemical Society.

[51]  Junliang Wu,et al.  Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions. , 2009, Journal of the American Chemical Society.

[52]  Koki Kato,et al.  Melanin-concentrating hormone receptor 1 antagonists. Synthesis and structure-activity relationships of novel 3-(aminomethyl)quinolines. , 2012, Journal of medicinal chemistry.

[53]  Shui-Tong Lee,et al.  Bipolar Molecule as an Excellent Hole-Transporter for Organic-Light Emitting Devices , 2009 .

[54]  Oxazolidinones as novel human CCR8 antagonists. , 2007, Bioorganic & medicinal chemistry letters.