Phosphane‐Mediated Domino Synthesis of Tetrasubstituted Furans from Simple Terminal Activated Olefins

Convenient and highly efficient syntheses of tetrasubstituted furans with flexible substituent patterns from simple and readily available starting materials have been developed. Under very mild conditions, with the mediation of stoichiometric nBu3P, simple terminal activated olefins and acyl chlorides or anhydrides smoothly furnish tetrasubstituted furans in modest to excellent yields. This synthetic strategy features a flexible selection of substituent pattern and a C-acylation/O-acylation/C-acylation/intramolecular Wittig reaction multiple domino assembly sequence.

[1]  A. Zarrelli,et al.  Regiodivergent synthesis of trisubstituted furans through Tf(2)O-catalyzed Friedel-Crafts acylation: a tool for access to tetrahydrofuran lignan analogues. , 2012, Organic & biomolecular chemistry.

[2]  Peng‐Fei Xu,et al.  A powerful cascade approach for expeditious synthesis of trifluoromethylated furans. , 2011, Organic letters.

[3]  Silong Xu,et al.  PBu3-mediated vinylogous Wittig reaction of α-methyl allenoates with aldehydes and mechanistic investigations. , 2011, The Journal of organic chemistry.

[4]  K. Gothelf,et al.  β-Olefination of 2-alkynoates leading to trisubstituted 1,3-dienes. , 2011, Organic letters.

[5]  Xiaofeng Tong,et al.  Phosphine-catalyzed [3+2] annulations of γ-functionalized butynoates and 1C,3O-bisnucleophiles: highly selective reagent-controlled pathways to polysubstituted furans. , 2011, Organic letters.

[6]  Wenwei Lin,et al.  Preparation of functional benzofurans, benzothiophenes, and indoles using ester, thioester, and amide via intramolecular Wittig reactions. , 2011, Organic letters.

[7]  Wenwei Lin,et al.  A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions. , 2011, Organic & biomolecular chemistry.

[8]  Chengyu Wang,et al.  Pd/Cu-catalyzed cascade Sonogashira coupling/cyclization reactions to highly substituted 3-formyl furans. , 2011, Organic & biomolecular chemistry.

[9]  Silong Xu,et al.  Phosphine-mediated diverse reactivity of γ-substituted allenoates with aldehydes: syntheses of highly functionalized chromans and (E,E)-1,3-dienes , 2011 .

[10]  Huanfeng Jiang,et al.  Synthesis of 2,5-disubstituted 3-iodofurans via palladium-catalyzed coupling and iodocyclization of terminal alkynes. , 2011, The Journal of organic chemistry.

[11]  Huanfeng Jiang,et al.  Nano-Cu(2)O-catalyzed formation of C-C and C-O bonds: one-pot domino process for regioselective synthesis of α-carbonyl Furans from electron-deficient alkynes and 2-yn-1-ols. , 2010, Chemistry.

[12]  Silong Xu,et al.  Stereoselective synthesis of 1,2,3,4-tetrasubstituted dienes from allenoates and aldehydes: an observation of phosphine-induced chemoselectivity. , 2010, Organic letters.

[13]  Y. S. Tran,et al.  Equilibrium between a vinylogous ylide and a phosphonium dienolate zwitterion: vinylogous Wittig olefination versus vinylogous aldol-type reaction. , 2010, Tetrahedron.

[14]  Wenwei Lin,et al.  Preparation of tetrasubstituted furans via intramolecular Wittig reactions with phosphorus ylides as intermediates. , 2010, Organic letters.

[15]  C. Fu,et al.  Synthesis of polysubstituted furans based on a stepwise Sonogashira coupling of (Z)-3-iodoalk-2-en-1-ols with terminal propargylic alcohols and subsequent Au(I)- or Pd(II)-catalyzed cyclization-aromatization via elimination of H2O. , 2010, The Journal of organic chemistry.

[16]  Zhengjie He,et al.  Wittig olefination between phosphine, aldehyde, and allylic carbonate: a general method for stereoselective synthesis of trisubstituted 1,3-dienes with highly variable substituents. , 2010, Organic letters.

[17]  Haibin Song,et al.  Phosphine-mediated stereoselective reductive cyclopropanation of alpha-substituted allenoates with aromatic aldehydes. , 2010, Organic letters.

[18]  Huanfeng Jiang,et al.  Synthetic approach to polysubstituted furans: an efficient addition/oxidative cyclization of alkynoates and 1,3-dicarbonyl compounds. , 2010, The Journal of organic chemistry.

[19]  C. Qi,et al.  Silver‐Catalyzed One‐Pot Cyclization Reaction of Electron‐ Deficient Alkynes and 2‐Yn‐1‐ols: An Efficient Domino Process to Polysubstituted Furans , 2010 .

[20]  D. Ma,et al.  Cu(I)/L-proline-catalyzed coupling of substituted 3-iodoprop-2-en-1-ols with 1-alkynes and subsequent cyclization: a convenient approach for synthesizing polysubstituted furans. , 2010, Chemistry, an Asian journal.

[21]  Zhengkun Yu,et al.  Palladium-catalyzed carbonylative cycloisomerization of gamma-propynyl-1,3-diketones: a concise route to polysubstituted furans. , 2009, The Journal of organic chemistry.

[22]  Chih-Hsiu Lin,et al.  Synthesis of benzo[c] and naphtho[c]heterocycle diesters and dinitriles via homoelongation. , 2009, The Journal of organic chemistry.

[23]  Silong Xu,et al.  Phosphine-mediated olefination between aldehydes and allenes: an efficient synthesis of trisubstituted 1,3-dienes with high E-selectivity. , 2009, Organic letters.

[24]  Huanfeng Jiang,et al.  Copper-catalyzed domino rearrangement/dehydrogenation oxidation/carbene oxidation for one-pot regiospecific synthesis of highly functionalized polysubstituted furans. , 2009, Organic letters.

[25]  J. Barluenga,et al.  Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes. , 2008, Journal of the American Chemical Society.

[26]  Zhengjie He,et al.  An Unexpected Phosphine-Mediated Olefination of Salicylaldehydes with α-Methyl Allenoate , 2008 .

[27]  J. Aurrecoechea,et al.  Palladium-catalyzed cyclization/Heck- and cyclization/conjugate-addition-type sequences in the preparation of polysubstituted furans. , 2008, The Journal of organic chemistry.

[28]  Yong‐Min Liang,et al.  Copper-Catalyzed [4 + 1] Cycloadditions of α,β-Acetylenic Ketones with Diazoacetates to Form Trisubstituted Furans , 2007 .

[29]  Zhuang-Ping Zhan,et al.  Copper(II) Triflate‐Catalyzed Nucleophilic Substitution of Propargylic Acetates with Enoxysilanes. A Straightforward Synthetic Route to Polysubstituted Furans , 2007 .

[30]  M. Morreale,et al.  Room temperature zinc chloride-catalyzed cycloisomerization of Alk-3-yn-1-ones: synthesis of substituted furans. , 2007, Organic letters.

[31]  P. Langer,et al.  Synthesis of 2-Alkenyl-3-(alkoxycarbonyl)furans Based on Feist−Benary Cyclocondensation of (2,4-Dioxobutylidene)phosphoranes with α-Haloketones and α-Chloracetaldehyde , 2006 .

[32]  S. Kirsch Syntheses of polysubstituted furans: recent developments. , 2006, Organic & biomolecular chemistry.

[33]  M. Taddei,et al.  Microwave‐Assisted Paal–Knorr Reaction – Three‐Step Regiocontrolled Synthesis of Polysubstituted Furans, Pyrroles and Thiophenes , 2005 .

[34]  Richard Brown Entwicklungen in der Furansynthese , 2005 .

[35]  H. Wong,et al.  Use of furans in synthesis of bioactive compounds , 2005 .

[36]  Jae Nyoung Kim,et al.  Synthesis of deuterium labeled compounds by KCN-assisted hydrolysis of phosphonium salts , 2004 .

[37]  M. Krische,et al.  Phosphine-mediated reductive condensation of gamma-acyloxy butynoates: a diversity oriented strategy for the construction of substituted furans. , 2004, Journal of the American Chemical Society.

[38]  S. Ma,et al.  Transition Metal-Catalyzed/Mediated Reaction of Allenes with a Nucleophilic Functionality Connected to the α-Carbon Atom , 2003 .

[39]  R. Lachicotte,et al.  Rapid synthesis of the 7-deoxy zaragozic acid core. , 2002, Organic letters.

[40]  N. Lawrence,et al.  Reaction of Baylis–Hillman products with Swern and Dess–Martin oxidants , 2001 .

[41]  B. A. Keay,et al.  Synthesis of multi-substituted furan rings: the role of silicon , 1999 .

[42]  S. Cacchi,et al.  Heterocycles via cyclization of alkynes promoted by organopalladium complexes , 1999 .

[43]  X. Hou,et al.  Regioselective syntheses of substituted furans , 1998 .

[44]  H. Wong,et al.  Regiospecific synthesis of 3,4-disubstituted furans and 3-substituted furans using 3,4-Bis(tri-n-butylstannyl)furan and 3-(tri-n-butylstannyl)f , 1994 .

[45]  B. Lipshutz Five-membered heteroaromatic rings as intermediates in organic synthesis , 1986 .

[46]  T. Eicher,et al.  Zur reaktionsweise von azomethin-oxiden, -iminen und -yliden mit triafulvenen : Ein ungewöhnliches verhalten von 1.3-dipolen , 1975 .

[47]  F. M. Dean Naturally Occurring Oxygen Ring Compounds , 1963 .