Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: an efficient and sustainable synthesis of 1,3,4'-tricarbonyl compounds

An efficient and sustainable synthesis of the otherwise difficult to obtain 1,3,4′-tricarbonyl compounds through a water mediated, TBAF·3H2O promoted unprecedented tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester has been developed. Remarkably enhanced reactivity and improved chemoselectivity by using water as the reaction medium was observed. The 1,3,4′-tricarbonyl compounds facilitate further versatile transformations, which underscores the importance of these products as synthetic intermediates.

[1]  O. Shimomura,et al.  Linear polystyrene-stabilized palladium nanoparticles-catalyzed C-C coupling reaction in water. , 2011, The Journal of organic chemistry.

[2]  S. Ng,,et al.  An environmentally benign approach for the synthesis of bifunctional sulfonamide-amide compounds viaisocyanide-based multicomponent reactions , 2011 .

[3]  M. Baghbanzadeh,et al.  Water-prompted synthesis of alkyl nitrile derivatives via Knoevenagel condensation and Michael addition reaction , 2011 .

[4]  Shuangxi Xing,et al.  Cu2O acting as a robust catalyst in CuAAC reactions: water is the required medium , 2011 .

[5]  Chao‐Jun Li,et al.  “On water”-promoted direct alkynylation of isatins catalyzed by NHC–silver complexes for the efficient synthesis of 3-hydroxy-3-ethynylindolin-2-ones , 2011 .

[6]  M. Arai,et al.  An effective medium of H2O and low-pressure CO2 for the selective hydrogenation of aromatic nitro compounds to anilines , 2011 .

[7]  M. Poyatos,et al.  Palladium Catalysts with Sulfonate-Functionalized-NHC Ligands for Suzuki−Miyaura Cross-Coupling Reactions in Water , 2011 .

[8]  Dinesh Kumar,et al.  Surfactant mediated oxygen reuptake in water for green aerobic oxidation: mass-spectrometric determination of discrete intermediates to correlate oxygen uptake with oxidation efficiency. , 2011, Chemical communications.

[9]  P. Bertus,et al.  Titanium-mediated synthesis of 1,4-diketones from Grignard reagents and acyl cyanohydrins. , 2010, Angewandte Chemie.

[10]  D. Custar,et al.  Pd-catalyzed carbonylative conjugate addition of dialkylzinc reagents to unsaturated carbonyls. , 2010, Organic letters.

[11]  N. Yan,et al.  Transition metal nanoparticle catalysis in green solvents , 2010 .

[12]  F. Felpin,et al.  Recyclable Heterogeneous Palladium Catalysts in Pure Water: Sustainable Developments in Suzuki, Heck, Sonogashira and Tsuji–Trost Reactions , 2010 .

[13]  A. Mortreux,et al.  Carbonylative 1,4-addition of potassium aryltrifluoroborates to vinyl ketones , 2009 .

[14]  G. Hammond,et al.  Synthesis of functionalized alpha,alpha-disubstituted beta-alkynyl esters from allenoates through an alkynylenolate intermediate. , 2008, Organic letters.

[15]  Le‐Ping Liu,et al.  Michael addition of allenoates to electron-deficient olefins: facile synthesis of 2-alkynyl-substituted glutaric acid derivatives. , 2008, Organic letters.

[16]  A. Wu,et al.  A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives. , 2008, The Journal of organic chemistry.

[17]  G. Hammond,et al.  Thermodynamically favored aldol reaction of propargyl or allenyl esters: regioselective synthesis of carbinol allenoates. , 2008, Angewandte Chemie.

[18]  S. Chankeshwara,et al.  “On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines , 2007 .

[19]  Y. Nishiyama,et al.  Synthesis of 1,4-diketones : reaction of α-bromo ketones with tetrakis(dimethylamino)ethylene (TDAE) , 2006 .

[20]  S. Chankeshwara,et al.  Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water. , 2006, Organic letters.

[21]  A. V. Butin Furan as a 1,3-diketone equivalent: the second type furan recyclization applied to indole synthesis , 2006 .

[22]  Gopal L. Khatik,et al.  Catalyst-Free Conjugated Addition of Thiols to α,β-Unsaturated Carbonyl Compounds in Water , 2006 .

[23]  C. Che,et al.  Gold(III) porphyrin-catalyzed cycloisomerization of allenones. , 2006, Organic letters.

[24]  A. Katritzky,et al.  γ,δ-Unsaturated β-Diketones by Acylation of Ketones , 2005 .

[25]  Chao-Jun Li,et al.  Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. , 2005, Chemical reviews.

[26]  M. Finn,et al.  "On water": unique reactivity of organic compounds in aqueous suspension. , 2005, Angewandte Chemie.

[27]  Wenjian Qian,et al.  Studies on t-BuOK-catalyzed Michael addition of 1,2-allenic ketones with 2-substituted diethyl malonates: highly selective synthesis of β,γ-unsaturated enones , 2005 .

[28]  Alex Maioli Recent Advances in the Chemistry of 1,3-Diketones: Structural Modifications and Synthetic Applications , 2003 .

[29]  A. Kel'in Recent Advances in the Synthesis of 1,3-Diketones , 2003 .

[30]  Shichao Yu,et al.  Studies on K2CO3-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate: Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones , 2003 .

[31]  Yongming Zhang,et al.  Formation of 1,4-diketones via bis-acylation of the conjugated carbon–carbon double bonds in acrylates, acrylamides, methyl vinyl ketone and styrenes with aroyl chlorides promoted by samarium metal in DMF , 2003 .

[32]  Junliang Zhang,et al.  Pd0-catalyzed coupling cyclization reaction of Aryl or 1-alkenyl halides with 1,2-allenyl ketones: scope and mechanism. An efficient assembly of 2,3,4-, 2,3,5-tri- and 2,3,4,5-tetrasubstituted furans. , 2003, Chemistry.

[33]  S. Raghavan,et al.  Solid-phase synthesis of 1,4-diketones by thiazolium salt promoted addition of aldehydes to chalcones , 2002 .

[34]  M. Ishar,et al.  Unusual [8 + 2] Annelation in the Reactions of Allenic Ester/Ketone-Derived 1,3-Dipoles with Tropone , 2000 .

[35]  N. D’alessandro,et al.  Structure-activity relationship studies of novel heteroretinoids: induction of apoptosis in the HL-60 cell line by a novel isoxazole-containing heteroretinoid. , 1999, Journal of medicinal chemistry.

[36]  K. Mikami,et al.  New Type of Photochemical Carbon Skeletal Rearrangement: Transformation of α,β-Unsaturated Carbonyl to 1,4-Dicarbonyl Compounds , 1998 .

[37]  A. Numata,et al.  OLEFIN-INSERTION REACTION BETWEEN THE CARBONYLS OF BENZILS; FORMATION OF 1,4-DIKETONES BY MICHAEL ADDITON CATALYZED BY CYANIDE ION , 1997 .

[38]  L. Paquette,et al.  Oxidative Coupling of the Enolate Anion of (1R)-(+)-Verbenone with Fe(III) and Cu(II) Salts. Two Modes of Conjoining This Bicyclic Ketone across a Benzene Ring , 1995 .

[39]  J. A. Marshall,et al.  Observations Regarding the Ag(I)-Catalyzed Conversion of Allenones to Furans , 1994 .

[40]  A. Echavarren,et al.  Palladium-Catalyzed Reductive Coupling of Acid Chlorides with .beta.-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects , 1994 .

[41]  T. Hirao,et al.  Oxovanadium-induced oxidative desilylation for the selective synthesis of 1,4-diketones , 1992 .

[42]  Yoshinori Yamamoto,et al.  Synthesis of 1,4-dicarbonyl compounds via the conjugate addition of a masked activated ester, ROCH(CN)2 , 1991 .

[43]  沈伟,et al.  Facile synthesis of 1,4-diketones via palladium complex catalyzed isomerization of alkynediols , 1991 .

[44]  T. Hudlický,et al.  Anionic approaches to the construction of cyclopentanoids , 1989 .

[45]  M. P. Sammes,et al.  The synthesis and chemistry of azolenines.1 , 1988 .

[46]  N. Kimpe,et al.  Dehydrodimerization of imines via α-bromoimines using lithium diisopropylamide , 1986 .

[47]  D. Seyferth,et al.  Direct nucleophilic 1,4-acylation of .alpha.,.beta.-unsaturated ketones and aldehydes via acylcuprate reagents , 1985 .

[48]  E. Corey,et al.  1,4 Addition of acyl groups to conjugated enones , 1969 .