A novel one-pot three-component synthesis of 3-halofurans and sequential Suzuki coupling.

A novel sequence of Sonogashira coupling and electrophilic addition to an ynone, with concomitant deprotection and cyclocondensation, opens a new one-pot synthesis of 3-halofurans; the method can be readily elaborated to a new sequential Sonogashira-addition-cyclocondensation-Suzuki reaction to furnish 2,3,5-trisubstituted furans in a one-pot fashion.

[1]  Richard C. D. Brown.  Developments in furan syntheses. , 2005, Angewandte Chemie.

[2]  J. L. Gleason,et al.  Two birds with one metallic stone: single-pot catalysis of fundamentally different transformations. , 2004, Angewandte Chemie.

[3]  T. Müller,et al.  A novel one-pot four-component access to tetrahydro-beta-carbolines by a coupling-amination-aza-annulation-Pictet-Spengler sequence (CAAPS). , 2004, Chemical communications.

[4]  Hoon Han,et al.  Cooperative multi-catalyst systems for one-pot organic transformations. , 2004, Chemical Society reviews.

[5]  R. Larock,et al.  Synthesis of Heterocycles via Palladium π-Olefin and π-Alkyne Chemistry , 2004 .

[6]  T. Müller,et al.  New entry to a three-component pyrimidine synthesis by TMS-Ynones via Sonogashira coupling. , 2003, Organic letters.

[7]  J. Hartwig,et al.  Understanding the coupling of heteroaromatic substrates: Synthesis, structures, and reductive eliminations of heteroarylpalladium amido complexes , 2003 .

[8]  M. Bagley,et al.  Highly efficient synthesis of pyrimidines under microwave-assisted conditions , 2003 .

[9]  T. Luh,et al.  Combining furan annulation, heck reaction, and Sonogashira coupling for the synthesis of oligoaryls. , 2002, Organic letters.

[10]  Y. Ling,et al.  Palladium Catalyzed Transformation of Acyclic Units to Furans , 2002 .

[11]  P. Dormer,et al.  An expedient synthesis of highly functionalized naphthyridones and quinolines from a common N-aryl pyridinone template. , 2002, Organic letters.

[12]  J. Falck,et al.  A convenient preparation of 3-substituted furans: synthesis of perillene and dendrolasin. , 2002, Organic letters.

[13]  B. Katzenellenbogen,et al.  Synthesis and biological evaluation of a novel series of furans: Ligands selective for estrogen receptor α , 2001 .

[14]  D. Knight,et al.  Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols , 2001 .

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

[16]  D. Knight,et al.  A brief synthesis of β-iodofurans , 1996 .

[17]  D. Obrecht.  Acid‐Catalyzed Cyclization Reactions of Substituted Acetylenic Ketones: A new Approach for the Synthesis of 3‐Halofurans, Flavones, and Styrylchromones , 1989 .

[18]  M. Hooper,et al.  Isatogens; 9. The Synthesis of Isatogens by the Oxidation of 2-Substituted 1-Hydroxyindoles , 1974 .