Iodocyclization of ethoxyethyl ethers to ynamides: an immediate construction to benzo[b]furans.

The iodocyclization of ethoxyethyl ethers to ynamides was completed within three seconds. The corresponding benzo[b]furans were obtained in high yields (84%-quant.) under mild conditions.

[1]  R. Hsung,et al.  Ynamides in ring forming transformations. , 2014, Accounts of chemical research.

[2]  T. Punniyamurthy,et al.  A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines. , 2013, Organic letters.

[3]  F. Rominger,et al.  From ynamides to highly substituted benzo[b]furans: gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates. , 2013, Chemistry.

[4]  Yongxian Liu,et al.  Cascade electrophilic iodocyclization: efficient preparation of 4-iodomethyl substituted tetrahydro-β-carbolines and formal synthesis of oxopropaline G. , 2013, Organic letters.

[5]  G. Lai,et al.  Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes , 2013 .

[6]  Takashi Okitsu,et al.  Substituent effect of bis(pyridines)iodonium complexes as iodinating reagents: control of the iodocyclization/oxidation process. , 2013, Chemistry.

[7]  K. Jiang,et al.  Synthesis of 3-alkyl- or 3-allenyl-2-amidobenzofurans via electrophilic cyclization of o-anisole-substituted ynamides with carbocations. , 2013, Organic letters.

[8]  A. Verma,et al.  Site-selective electrophilic cyclization and subsequent ring-opening: a synthetic route to pyrrolo[1,2-a]quinolines and indolizines. , 2012, The Journal of organic chemistry.

[9]  R. Larock,et al.  An iodocyclization approach to substituted 3-iodothiophenes. , 2012, The Journal of organic chemistry.

[10]  G. Lushington,et al.  Solution-phase synthesis of a highly substituted furan library. , 2012, ACS combinatorial science.

[11]  Metin Zora,et al.  Synthesis of pyrazoles via electrophilic cyclization. , 2011, The Journal of organic chemistry.

[12]  C. Cho,et al.  Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling. , 2011, ACS combinatorial science.

[13]  T. M. Potewar,et al.  Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles. , 2011, The Journal of organic chemistry.

[14]  C. Cho,et al.  Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans. , 2011, ACS combinatorial science.

[15]  Benhur Godoi,et al.  Synthesis of heterocycles via electrophilic cyclization of alkynes containing heteroatom. , 2011, Chemical reviews.

[16]  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.

[17]  P. Toullec,et al.  Room-temperature metal-free electrophilic 5-endo-selective iodocarbocyclization of 1,5-enynes. , 2010, Organic letters.

[18]  R. Hsung,et al.  Ynamides: a modern functional group for the new millennium. , 2010, Chemical reviews.

[19]  A. Kuzmin,et al.  Nucleophilic cycloaromatization of ynamide-terminated enediynes. , 2010, The Journal of organic chemistry.

[20]  Takashi Okitsu,et al.  Reagent-controlled oxidative aromatization in iodocyclization: switchable access to dihydropyrazoles and pyrazoles. , 2010, Organic letters.

[21]  G. Evano,et al.  Ynamides: versatile tools in organic synthesis. , 2010, Angewandte Chemie.

[22]  G. Zeni,et al.  Synthesis of 2,3-dihydroselenophene and selenophene derivatives by electrophilic cyclization of homopropargyl selenides. , 2010, Organic letters.

[23]  C. Cho,et al.  Diverse methyl sulfone-containing benzo[b]thiophene library via iodocyclization and palladium-catalyzed coupling. , 2010, Journal of combinatorial chemistry.

[24]  R. Larock,et al.  Iodine/palladium approaches to the synthesis of polyheterocyclic compounds. , 2010, The Journal of organic chemistry.

[25]  M. Mphahlele Molecular Iodine-Mediated Cyclization of Tethered Heteroatom-Containing Alkenyl or Alkynyl Systems , 2009, Molecules.

[26]  D. Rodríguez,et al.  Iodoarylation reactions of allenes: inter- and intramolecular processes. , 2009, Chemistry.

[27]  Benhur Godoi,et al.  Synthesis of organochalcogen propargyl aryl ethers and their application in the electrophilic cyclization reaction: an efficient preparation of 3-halo-4-chalcogen-2H-benzopyrans. , 2009, The Journal of organic chemistry.

[28]  F. Manarin,et al.  Electrophilic cyclization of 2-chalcogenealkynylanisoles: versatile access to 2-chalcogen-benzo[b]furans. , 2009, The Journal of organic chemistry.

[29]  G. Lushington,et al.  Parallel synthesis of a multi-substituted benzo[b]furan library. , 2008, Journal of combinatorial chemistry.

[30]  Takashi Okitsu,et al.  Iodocyclization of ethoxyethyl ethers to alkynes: a broadly applicable synthesis of 3-iodobenzo[b]furans. , 2008, Organic letters.

[31]  J. Bats,et al.  Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives. , 2008, Chemistry.

[32]  S. Stahl,et al.  Copper-catalyzed aerobic oxidative amidation of terminal alkynes: efficient synthesis of ynamides. , 2008, Journal of the American Chemical Society.

[33]  A. Hashmi,et al.  Gold-Catalyzed Cyclization of N-Alkynyl Carbamates , 2007 .

[34]  R. Hsung,et al.  A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans. , 2007, Organic letters.

[35]  Y. Kita,et al.  Reaction of Tetrahydropyranyl Ethers with Triethylsilyl Trifluoromethanesulfonate–2,4,6‐Collidine Combination: Speculation on the Intermediate, Efficient Deprotection, and Application to Efficient Ring‐Closing Metathesis as a Tether , 2007 .

[36]  H. Togo,et al.  Synthetic Use of Molecular Iodine for Organic Synthesis , 2006 .

[37]  Henar Vázquez-Villa,et al.  The reaction of o-alkynylarene and heteroarene carboxaldehyde derivatives with iodonium ions and nucleophiles: a versatile and regioselective synthesis of 1H-isochromene, naphthalene, indole, benzofuran, and benzothiophene compounds. , 2006, Chemistry.

[38]  M. Trincado,et al.  Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4: synthesis of benzocyclic ketones. , 2006, Angewandte Chemie.

[39]  R. Hsung,et al.  Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides. An intramolecular amidation for the synthesis of macrocyclic ynamides. , 2006, The Journal of organic chemistry.

[40]  Y. Kita,et al.  Reaction of the acetals with TESOTf-base combination; speculation of the intermediates and efficient mixed acetal formation. , 2006, Journal of the American Chemical Society.

[41]  R. Larock,et al.  Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization. , 2005, The Journal of organic chemistry.

[42]  Richard C. Larock,et al.  Synthesis of Heterocycles and Carbocycles by Electrophilic Cyclization of Alkynes , 2005 .

[43]  F. Colobert,et al.  Palladium‐Catalyzed Suzuki Coupling with Terminal Alkynes – Application to the Synthesis of 2,3‐Disubstituted Benzo[b]furans , 2005 .

[44]  A. Ballesteros,et al.  Intramolecular iodoarylation reaction of alkynes: easy access to derivatives of benzofused heterocycles. , 2005, Chemical communications.

[45]  J. Barluenga,et al.  Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4): a versatile oxidizing reagent. , 2004, Chemistry.

[46]  T. Wirth,et al.  Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications. , 2004, Chemical Society reviews.

[47]  M. Trincado,et al.  Intramolecular arylation reactions of alkenes: a flexible approach to chromans and tetrahydroquinoline derivatives. , 2004, Journal of the American Chemical Society.

[48]  Henar Vázquez-Villa,et al.  Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles. , 2003, Journal of the American Chemical Society.

[49]  M. Trincado,et al.  IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: direct assembly of 3-iodoindole cores. , 2003, Angewandte Chemie.

[50]  G. Fabrizi,et al.  A New Approach to 2,3-Disubstituted Benzo[b]furans from o-Alkynylphenols via 5-endo-dig-Iodocyclisation/Palladium-Catalysed Reactions , 1999 .

[51]  G. Asensio,et al.  Regio- and stereoselective iodofluorination of alkenes with bis(pyridine)iodonium(I) tetrafluoroborate , 1991 .

[52]  Miguel A. Rodríguez,et al.  ELECTROPHILIC ADDITIONS OF POSITIVE IODINE TO ALKYNES THROUGH AN IODONIUM MECHANISM , 1990 .

[53]  G. Asensio,et al.  I(py)2BF4, a New Reagent in Organic Synthesis: General Method for the 1,2‐Iodofunctionalization of Olefins , 1985 .