Literature DB >> 20046214

Incorporation of hexafluorobutyne into furans or phenols via reaction with iron(0) carbene or vinylketene complexes.

Ravish K Akhani1, Wayne F K Schnatter.   

Abstract

Reaction of iron(0) carbene complexes with hexafluorobut-2-yne produces 3,4-bis(trifluoromethylated)furans in a process that is favored for electron rich carbenes. No traces of furannulation or benzannulation are observed with Group 6 Fischer carbenes. Reaction of hexafluorobut-2-yne with a vinylketene iron(0) complex gives a 2,3-bis-trifluoromethylated phenol.

Entities:  

Year:  2009        PMID： 20046214      PMCID： PMC2629604          DOI： 10.1016/j.tetlet.2008.12.037

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

1.  Generation and reaction of metal-containing carbonyl ylides: tandem [3 + 2]-cycloaddition--carbene insertion leading to novel polycyclic compounds.

Authors:  N Iwasawa; M Shido; H Kusama
Journal:  J Am Chem Soc       Date:  2001-06-20       Impact factor: 15.419

2.  Update 1 of: Asymmetric fluorination, trifluoromethylation, and perfluoroalkylation reactions.

Authors:  Jun-An Ma; Dominique Cahard
Journal:  Chem Rev       Date:  2008-09       Impact factor: 60.622

3.  The many roles for fluorine in medicinal chemistry.

Authors:  William K Hagmann
Journal:  J Med Chem       Date:  2008-06-21       Impact factor: 7.446

4.  Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes.

Authors:  José Barluenga; Lorena Riesgo; Rubén Vicente; Luis A López; Miguel Tomás
Journal:  J Am Chem Soc       Date:  2008-09-19       Impact factor: 15.419

5.  Catalytic transmetalation from group 6 Fischer carbene complexes: an emerging powerful tool in organic synthesis.

Authors:  Mar Gómez-Gallego; María José Mancheño; Miguel A Sierra
Journal:  Acc Chem Res       Date:  2005-01       Impact factor: 22.384

6.  Novel approach for catalytic cyclopropanation of alkenes via (2-furyl)carbene complexes from 1-benzoyl-cis-1-buten-3-yne.

Authors:  Koji Miki; Fumiaki Nishino; Kouichi Ohe; Sakae Uemura
Journal:  J Am Chem Soc       Date:  2002-05-15       Impact factor: 15.419

7.  Furan forming reactions of cis-2-alken-4-yn-1-ones.

Authors:  Charles P Casey; Neil A Strotman
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

8.  Chromene chromium carbene complexes in the syntheses of naphthopyran and naphthopyrandione units present in photochromic materials and biologically active natural products.

Authors:  Manish Rawat; Victor Prutyanov; William D Wulff
Journal:  J Am Chem Soc       Date:  2006-08-30       Impact factor: 15.419

9.  Alpha-trifluoromethylated carbanion synthons.

Authors:  Kenji Uneyama; Toshimasa Katagiri; Hideki Amii
Journal:  Acc Chem Res       Date:  2008-06-14       Impact factor: 22.384

10.  Pentakis(trifluoromethyl)phenyl, a sterically crowded and electron-withdrawing group: synthesis and acidity of pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline.

Authors:  Agnes Kütt; Valeria Movchun; Toomas Rodima; Timo Dansauer; Eduard B Rusanov; Ivo Leito; Ivari Kaljurand; Juta Koppel; Viljar Pihl; Ivar Koppel; Gea Ovsjannikov; Lauri Toom; Masaaki Mishima; Maurice Medebielle; Enno Lork; Gerd-Volker Röschenthaler; Ilmar A Koppel; Alexander A Kolomeitsev
Journal:  J Org Chem       Date:  2008-03-07       Impact factor: 4.354
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  1 in total

1.  Halogenated catechols from cycloaddition reactions of η-(2-ethoxyvinylketene)iron(0) complexes with 1-haloalkynes.

Authors:  Jimmy Truong; Vioela Caze; Ravish K Akhani; Gayatribahen K Joshi; Lazaros Kakalis; Nikita Matsunaga; Wayne F K Schnatter
Journal:  Tetrahedron Lett       Date:  2010-02-10       Impact factor: 2.415
  1 in total

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