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Volumn 54, Issue 1, 2011, Pages 95-102

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides

Author keywords

alkene; alkyne; fluorine; radical fluoroalkylation; sulfonamide

Indexed keywords

ALKENE; ALKYNE; CATALYTIC AMOUNTS; RADICAL ATOMS; RADICAL FLUOROALKYLATION; SODIUM DITHIONITE; SULFONAMIDE; TERMINAL ALKENES; TRIETHYLBORANE;

EID: 79251559106     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4139-0     Document Type: Conference Paper
Times cited : (9)

References (28)
  • 1
    • 34848848499 scopus 로고    scopus 로고
    • Fluorine in pharmaceuticals: Looking beyond intuition
    • 1:CAS:528:DC%2BD2sXhtVOlt7rN 10.1126/science.1131943
    • K. Mueller C. Faeh F. Diederich 2007 Fluorine in pharmaceuticals: Looking beyond intuition Science 317 1881 1886 1:CAS:528:DC%2BD2sXhtVOlt7rN 10.1126/science.1131943
    • (2007) Science , vol.317 , pp. 1881-1886
    • Mueller, K.1    Faeh, C.2    Diederich, F.3
  • 2
    • 38149016915 scopus 로고    scopus 로고
    • Understanding organofluorine chemistry. An introduction to the C-F bond
    • 10.1039/b711844a
    • D. O'Hagan 2008 Understanding organofluorine chemistry. An introduction to the C-F bond Chem Soc Rev 37 308 319 10.1039/b711844a
    • (2008) Chem Soc Rev , vol.37 , pp. 308-319
    • O'Hagan, D.1
  • 3
    • 38149070200 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry
    • 1:CAS:528:DC%2BD1cXmtVGgsw%3D%3D 10.1039/b610213c
    • S. Purser P.R. Moore S. Swallow V. Gouverneur 2008 Fluorine in medicinal chemistry Chem Soc Rev 37 320 330 1:CAS:528:DC%2BD1cXmtVGgsw%3D%3D 10.1039/b610213c
    • (2008) Chem Soc Rev , vol.37 , pp. 320-330
    • Purser, S.1    Moore, P.R.2    Swallow, S.3    Gouverneur, V.4
  • 4
    • 49449097238 scopus 로고    scopus 로고
    • The many roles for fluorine in medicinal chemistry
    • 1:CAS:528:DC%2BD1cXns1WjtLo%3D 10.1021/jm800219f
    • W.K. Hagmann 2008 The many roles for fluorine in medicinal chemistry J Med Chem 51 4359 4369 1:CAS:528:DC%2BD1cXns1WjtLo%3D 10.1021/jm800219f
    • (2008) J Med Chem , vol.51 , pp. 4359-4369
    • Hagmann, W.K.1
  • 5
    • 4544369746 scopus 로고    scopus 로고
    • The unique role of fluorine in the design of active ingredients for modern crop protection
    • 1:CAS:528:DC%2BD2cXjvFeqtLw%3D 10.1002/cbic.200300833
    • P. Jeschke 2004 The unique role of fluorine in the design of active ingredients for modern crop protection ChemBioChem 5 570 589 1:CAS:528:DC%2BD2cXjvFeqtLw%3D 10.1002/cbic.200300833
    • (2004) ChemBioChem , vol.5 , pp. 570-589
    • Jeschke, P.1
  • 6
    • 75749113386 scopus 로고    scopus 로고
    • Fluorine & chirality: How to create a nonracemic stereogenic carbon-fluorine center
    • 1:CAS:528:DC%2BC3cXht1Wltbg%3D 10.1039/b909566g
    • D. Cahard X. Xu S. Couve-Bonnaire X. Pannecoucke 2010 Fluorine & chirality: How to create a nonracemic stereogenic carbon-fluorine center Chem Soc Rev 39 558 568 1:CAS:528:DC%2BC3cXht1Wltbg%3D 10.1039/b909566g
    • (2010) Chem Soc Rev , vol.39 , pp. 558-568
    • Cahard, D.1    Xu, X.2    Couve-Bonnaire, S.3    Pannecoucke, X.4
  • 7
    • 72149122065 scopus 로고    scopus 로고
    • Selective difluoromethylation and monofluoromethylation reactions
    • Hu J, Zhang W, Wang F. Selective difluoromethylation and monofluoromethylation reactions. Chem Commun, 2009, 7465-7478
    • (2009) Chem Commun , pp. 7465-7478
    • Hu, J.1    Zhang, W.2    Wang, F.3
  • 8
    • 46149094509 scopus 로고    scopus 로고
    • Fluorination in medicinal chemistry: Methods, strategies, and recent developments
    • 1:CAS:528:DC%2BD1cXhtFShurw%3D 10.1021/op700134j
    • K.L. Kirk 2008 Fluorination in medicinal chemistry: Methods, strategies, and recent developments Org Proc Res Dev 12 305 321 1:CAS:528: DC%2BD1cXhtFShurw%3D 10.1021/op700134j
    • (2008) Org Proc Res Dev , vol.12 , pp. 305-321
    • Kirk, K.L.1
  • 10
    • 4544240958 scopus 로고    scopus 로고
    • Halogenation of drugs enhances membrane binding and permeation
    • 1:CAS:528:DC%2BD2cXjvFeqtbw%3D
    • G. Gerebtzoff X. Li-Blatter H. Fischer A. Frentzel A. Seelig 2004 Halogenation of drugs enhances membrane binding and permeation Chem-BioChem 5 676 684 1:CAS:528:DC%2BD2cXjvFeqtbw%3D
    • (2004) Chem-BioChem , vol.5 , pp. 676-684
    • Gerebtzoff, G.1    Li-Blatter, X.2    Fischer, H.3    Frentzel, A.4    Seelig, A.5
  • 11
    • 4544288081 scopus 로고    scopus 로고
    • Probing the proteolytic stability of β-peptides containing α-fluoro- and α-hydroxy-β-amino acids
    • 1:CAS:528:DC%2BD2cXjvFeqtbo%3D 10.1002/cbic.200300827
    • D.F. Hook F. Gessier C. Noti P. Kast D. Seebach 2004 Probing the proteolytic stability of β-peptides containing α-fluoro- and α-hydroxy-β-amino acids ChemBioChem 5 691 706 1:CAS:528: DC%2BD2cXjvFeqtbo%3D 10.1002/cbic.200300827
    • (2004) ChemBioChem , vol.5 , pp. 691-706
    • Hook, D.F.1    Gessier, F.2    Noti, C.3    Kast, P.4    Seebach, D.5
  • 12
    • 4544318450 scopus 로고    scopus 로고
    • Fluorine interactions at the thrombin active site: Protein backbone fragments H-C(α)-C=O comprise a favorable C-F environment and interactions of C-F with elec trophiles
    • 1:CAS:528:DC%2BD2cXjvFeqtb8%3D 10.1002/cbic.200300907
    • J.A. Olsen D.W. Banner P. Seiler B. Wagner T. Tschopp U. Obst-Sander M. Kansy K. Muller F. Diederich 2004 Fluorine interactions at the thrombin active site: Protein backbone fragments H-C(α)-C=O comprise a favorable C-F environment and interactions of C-F with elec trophiles ChemBioChem 5 666 675 1:CAS:528:DC%2BD2cXjvFeqtb8%3D 10.1002/cbic.200300907
    • (2004) ChemBioChem , vol.5 , pp. 666-675
    • Olsen, J.A.1    Banner, D.W.2    Seiler, P.3    Wagner, B.4    Tschopp, T.5    Obst-Sander, U.6    Kansy, M.7    Muller, K.8    Diederich, F.9
  • 13
    • 9444267656 scopus 로고    scopus 로고
    • Synthesis of α-fluorosulfonamides by electrophilic fluorination
    • 1:CAS:528:DC%2BD2cXotlaltr0%3D 10.1021/ol048249z
    • B. Hill Y. Liu S.D. Yaylor 2004 Synthesis of α-fluorosulfonamides by electrophilic fluorination Org Lett 6 4285 4288 1:CAS:528: DC%2BD2cXotlaltr0%3D 10.1021/ol048249z
    • (2004) Org Lett , vol.6 , pp. 4285-4288
    • Hill, B.1    Liu, Y.2    Yaylor, S.D.3
  • 15
    • 0016606370 scopus 로고
    • Antiinflammatory fluoroalkanesul fonanilides. Other fluoroalkanesulfonamido diaryl systems
    • 1:CAS:528:DyaE2MXhs1Cksr0%3D 10.1021/jm00238a013
    • G.G.I. Moore J.K. Harrington 1975 Antiinflammatory fluoroalkanesul fonanilides. Other fluoroalkanesulfonamido diaryl systems J Med Chem 18 386 391 1:CAS:528:DyaE2MXhs1Cksr0%3D 10.1021/jm00238a013
    • (1975) J Med Chem , vol.18 , pp. 386-391
    • Moore, G.G.I.1    Harrington, J.K.2
  • 16
    • 75849162556 scopus 로고    scopus 로고
    • Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase
    • 1:CAS:528:DC%2BC3cXhvF2qs7k%3D 10.1016/j.ejmech.2009.11.052
    • Z. Benfodda F. Guillen B. Romestand A. Dahmani H. Blancou 2010 Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase Eur J Med Chem 45 1225 1229 1:CAS:528:DC%2BC3cXhvF2qs7k%3D 10.1016/j.ejmech.2009.11.052
    • (2010) Eur J Med Chem , vol.45 , pp. 1225-1229
    • Benfodda, Z.1    Guillen, F.2    Romestand, B.3    Dahmani, A.4    Blancou, H.5
  • 17
    • 33749988707 scopus 로고    scopus 로고
    • Enantioselective synthesis of protected L-4-[sulfonamide(difluoromethyl)] phenylalanine and an examination of hexa- and tripeptide platforms for evaluating pTyr Mimics for PTP1B Inhibition
    • 1:CAS:528:DC%2BD28XpslWntr8%3D 10.1021/jo061496r
    • B. Hill V. Ahmed D. Bates S.D. Taylor 2006 Enantioselective synthesis of protected L-4-[sulfonamide(difluoromethyl)]phenylalanine and an examination of hexa- and tripeptide platforms for evaluating pTyr Mimics for PTP1B Inhibition J Org Chem 71 8190 8197 1:CAS:528:DC%2BD28XpslWntr8%3D 10.1021/jo061496r
    • (2006) J Org Chem , vol.71 , pp. 8190-8197
    • Hill, B.1    Ahmed, V.2    Bates, D.3    Taylor, S.D.4
  • 18
    • 33846010139 scopus 로고    scopus 로고
    • Synthesis of α-fluorosulfonate and α-fluorosulfonamide analogues of a sulfated carbohydrate
    • 1:CAS:528:DC%2BD28Xht1Clu7%2FO 10.1021/ol062357z
    • L. Navidpour W. Lu S.D. Taylor 2006 Synthesis of α-fluorosulfonate and α-fluorosulfonamide analogues of a sulfated carbohydrate Org Lett 8 5617 5620 1:CAS:528:DC%2BD28Xht1Clu7%2FO 10.1021/ol062357z
    • (2006) Org Lett , vol.8 , pp. 5617-5620
    • Navidpour, L.1    Lu, W.2    Taylor, S.D.3
  • 19
    • 33845388351 scopus 로고    scopus 로고
    • Introducing difluoromethylene sulfonamide group via nucleophilic addition of difluoromethylene anion with aromatic aldehydes
    • 1:CAS:528:DC%2BD28XhtlagtrnE 10.1016/j.tet.2006.11.036
    • J.L. Li J.T. Liu 2007 Introducing difluoromethylene sulfonamide group via nucleophilic addition of difluoromethylene anion with aromatic aldehydes Tetrahedron 63 898 903 1:CAS:528:DC%2BD28XhtlagtrnE 10.1016/j.tet.2006.11.036
    • (2007) Tetrahedron , vol.63 , pp. 898-903
    • Li, J.L.1    Liu, J.T.2
  • 20
    • 0000836901 scopus 로고    scopus 로고
    • Structure, reactivity, and chemistry of fluoroalkyl radicals
    • 1:CAS:528:DyaK28XktFOqsb4%3D 10.1021/cr941142c
    • W.R. Dolbier Jr. 1996 Structure, reactivity, and chemistry of fluoroalkyl radicals Chem Rev 96 1557 1584 1:CAS:528:DyaK28XktFOqsb4%3D 10.1021/cr941142c
    • (1996) Chem Rev , vol.96 , pp. 1557-1584
    • Dolbier, Jr.W.R.1
  • 21
    • 34547100278 scopus 로고    scopus 로고
    • Radical (phenylsulfonyl)difluoromethylation with iododifluoromethyl phenyl sulfone
    • 1:CAS:528:DC%2BD2sXmslyqs7g%3D 10.1021/jo070618s
    • Y. Li J. Liu L. Zhang L. Zhu J. Hu 2007 Radical (phenylsulfonyl) difluoromethylation with iododifluoromethyl phenyl sulfone J Org Chem 72 5824 5827 1:CAS:528:DC%2BD2sXmslyqs7g%3D 10.1021/jo070618s
    • (2007) J Org Chem , vol.72 , pp. 5824-5827
    • Li, Y.1    Liu, J.2    Zhang, L.3    Zhu, L.4    Hu, J.5
  • 22
    • 56949093280 scopus 로고    scopus 로고
    • 2H-substituted alkenes
    • 1:CAS:528:DC%2BD1cXhsVOntLbM 10.1016/j.tet.2008.11.011
    • 2H-substituted alkenes Tetrahedron 65 478 483 1:CAS:528:DC%2BD1cXhsVOntLbM 10.1016/j.tet.2008. 11.011
    • (2009) Tetrahedron , vol.65 , pp. 478-483
    • Li, Y.1    Li, H.2    Hu, J.3
  • 23
    • 9444297821 scopus 로고    scopus 로고
    • Nucleophilic difluoromethylation of primary alkyl halides using difluoromethyl phenyl sulfone as a difluoromethyl anion synthon
    • 10.1021/ol048166i
    • G.K.S. Prakash J. Hu Y. Wang G.A. Olah 2003 Nucleophilic difluoromethylation of primary alkyl halides using difluoromethyl phenyl sulfone as a difluoromethyl anion synthon Org Lett 6 4315 4317 10.1021/ol048166i
    • (2003) Org Lett , vol.6 , pp. 4315-4317
    • Prakash, G.K.S.1    Hu, J.2    Wang, Y.3    Olah, G.A.4
  • 24
    • 84912581261 scopus 로고
    • Perfluoro- and polyfluorosulfonic acids. XIV. Formation of difluorocarbene from difluoromethanesulfonyl fluoride with nucleophiles
    • Chen QY, Zhu SZ. Perfluoro- and polyfluorosulfonic acids. XIV. Formation of difluorocarbene from difluoromethanesulfonyl fluoride with nucleophiles. Org Chem, 1984, 434-439
    • (1984) Org Chem , pp. 434-439
    • Chen, Q.Y.1    Zhu, S.Z.2
  • 25
    • 10844260602 scopus 로고
    • Perfluoro- and polyfluorosulfonic acids. XVIII. Formation of difluorocarbene from derivatives of difluoromethanesulfonyl fluoride
    • 1:CAS:528:DyaL28XlslWku7o%3D
    • Q.Y. Chen S.Z. Zhu 1986 Perfluoro- and polyfluorosulfonic acids. XVIII. Formation of difluorocarbene from derivatives of difluoromethanesulfonyl fluoride J Chinese Chem Soc 44 92 96 1:CAS:528:DyaL28XlslWku7o%3D
    • (1986) J Chinese Chem Soc , vol.44 , pp. 92-96
    • Chen, Q.Y.1    Zhu, S.Z.2
  • 26
    • 79251543803 scopus 로고
    • Perfluoro- and polyfluoroalkanesulfonic acids. XIX. Effect of reaction conditions on the formation of difluorocarbene from difluoromethanesulfonyl fluoride
    • 1:CAS:528:DyaL2sXhtF2ht74%3D
    • Q.Y. Chen S.Z. Zhu 1986 Perfluoro- and polyfluoroalkanesulfonic acids. XIX. Effect of reaction conditions on the formation of difluorocarbene from difluoromethanesulfonyl fluoride J Chinese Chem Soc 44 742 745 1:CAS:528:DyaL2sXhtF2ht74%3D
    • (1986) J Chinese Chem Soc , vol.44 , pp. 742-745
    • Chen, Q.Y.1    Zhu, S.Z.2
  • 27
    • 0036401437 scopus 로고    scopus 로고
    • 2: Preparation and application in asymmetric alkynylation of aldehydes
    • 2: Preparation and application in asymmetric alkynylation of aldehydes. Chem Commun, 2002, 2098-2099
    • (2002) Chem Commun , pp. 2098-2099
    • Chen, Z.1    Xiong, W.2    Jiang, B.3
  • 28
    • 0033444618 scopus 로고    scopus 로고
    • The sulfinatodehalogenation reaction
    • 1:CAS:528:DyaK1MXltlegsr4%3D
    • W.Y. Huang F.H. Wu 1999 The sulfinatodehalogenation reaction Isr J Chem 39 167 170 1:CAS:528:DyaK1MXltlegsr4%3D
    • (1999) Isr J Chem , vol.39 , pp. 167-170
    • Huang, W.Y.1    Wu, F.H.2


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