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Efficient direct 2,2,2-trifluoroethylation of indoles via C-H functionalization
被引:67
作者:

Tolnai, Gergely L.
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Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Szekely, Anna
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Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Mako, Zita
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Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Gati, Tamas
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Servier Res Inst Med Chem, H-1031 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Daru, Janos
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Hungarian Acad Sci, Res Ctr Nat Sci, Dept Theoret Chem, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Bihari, Tamas
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Hungarian Acad Sci, Res Ctr Nat Sci, Dept Theoret Chem, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Stirling, Andras
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Hungarian Acad Sci, Res Ctr Nat Sci, Dept Theoret Chem, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary

Novak, Zoltan
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Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary
机构:
[1] Eotvos Lorand Univ, Fac Sci, Inst Chem, MTA ELTE Lendulet Catalysis & Organ Synth Res Grp, H-1117 Budapest, Hungary
[2] Servier Res Inst Med Chem, H-1031 Budapest, Hungary
[3] Hungarian Acad Sci, Res Ctr Nat Sci, Dept Theoret Chem, H-1117 Budapest, Hungary
关键词:
COPPER-CATALYZED TRIFLUOROMETHYLTHIOLATION;
CROSS-COUPLING REACTIONS;
DIARYLIODONIUM SALTS;
DIRECT ALKYNYLATION;
ALKYNES;
ARYL;
TRIFLUOROETHYLATION;
ALDEHYDES;
REAGENTS;
ALKENES;
D O I:
10.1039/c5cc00519a
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
A novel highly C3 selective metal free trifluoroethylation of indoles using 2,2,2-trifuoroethyl(mesityl)-iodonium triflate was developed. The methodology enables the introduction of a trifluoroethyl group in a fast and efficient reaction under mild conditions with high functional group tolerance. Beyond the synthetic developments, quantum chemical calculations provide a deeper understanding of the transformation.
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页码:4488 / 4491
页数:4
相关论文
共 74 条
[1]
Electrophilic Trifluoromethylthiolation of Carbonyl Compounds
[J].
Alazet, Sebastien
;
Zimmer, Luc
;
Billard, Thierry
.
CHEMISTRY-A EUROPEAN JOURNAL,
2014, 20 (28)
:8589-8593

Alazet, Sebastien
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, F-69622 Villeurbanne, France
Grp Hosp Est, CERMEP In Vivo Imaging, F-69003 Lyon, France Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, F-69622 Villeurbanne, France

Zimmer, Luc
论文数: 0 引用数: 0
h-index: 0
机构:
Grp Hosp Est, CERMEP In Vivo Imaging, F-69003 Lyon, France
Grp Hosp Est, Lyon Neurosci Res Ctr, UMR CNRS 5292, UMR INSERM 1028, F-69003 Lyon, France Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, F-69622 Villeurbanne, France

Billard, Thierry
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, F-69622 Villeurbanne, France
Grp Hosp Est, CERMEP In Vivo Imaging, F-69003 Lyon, France Univ Lyon 1, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS, F-69622 Villeurbanne, France
[2]
ON THE REACTIVITY OF CFNH3-NCH2X (N = 0, 1, 2, AND 3, AND X = H OR HALOGEN ATOM)
[J].
BODOR, N
;
HUANG, MJ
;
SZANTAY, C
;
SZANTAY, C
.
TETRAHEDRON,
1992, 48 (28)
:5823-5830

BODOR, N
论文数: 0 引用数: 0
h-index: 0
机构: GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,PHYS CHEM RES DEPT,H-1475 BUDAPEST,HUNGARY

HUANG, MJ
论文数: 0 引用数: 0
h-index: 0
机构: GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,PHYS CHEM RES DEPT,H-1475 BUDAPEST,HUNGARY

SZANTAY, C
论文数: 0 引用数: 0
h-index: 0
机构: GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,PHYS CHEM RES DEPT,H-1475 BUDAPEST,HUNGARY

SZANTAY, C
论文数: 0 引用数: 0
h-index: 0
机构: GEDEON RICHTER CHEM WORKS LTD,CHEM WORKS,PHYS CHEM RES DEPT,H-1475 BUDAPEST,HUNGARY
[3]
One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
[J].
Brand, Jonathan P.
;
Chevalley, Clara
;
Waser, Jerome
.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,
2011, 7
:565-569

Brand, Jonathan P.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

Chevalley, Clara
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland

Waser, Jerome
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSO, Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, CH-1015 Lausanne, Switzerland
[4]
Direct Alkynylation of Indole and Pyrrole Heterocycles
[J].
Brand, Jonathan P.
;
Charpentier, Julie
;
Waser, Jerome
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2009, 48 (49)
:9346-9349

Brand, Jonathan P.
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland

Charpentier, Julie
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland

Waser, Jerome
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland
[5]
Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents
[J].
Charpentier, Julie
;
Frueh, Natalja
;
Togni, Antonio
.
CHEMICAL REVIEWS,
2015, 115 (02)
:650-682

Charpentier, Julie
论文数: 0 引用数: 0
h-index: 0
机构:
Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

Frueh, Natalja
论文数: 0 引用数: 0
h-index: 0
机构:
Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland

Togni, Antonio
论文数: 0 引用数: 0
h-index: 0
机构:
Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland Swiss Fed Inst Technol, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
[6]
Copper-Catalyzed Arylative Meyer-Schuster Rearrangement of Propargylic Alcohols to Complex Enones Using Diaryliodonium Salts
[J].
Collins, Beatrice S. L.
;
Suero, Marcos G.
;
Gaunt, Matthew J.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2013, 52 (22)
:5799-5802

Collins, Beatrice S. L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

论文数: 引用数:
h-index:
机构:

Gaunt, Matthew J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[7]
Sandmeyer trifluoromethylthiolation of arenediazonium salts with sodium thiocyanate and Ruppert-Prakash reagent
[J].
Danoun, Gregory
;
Bayarmagnai, Bilguun
;
Gruenberg, Matthias F.
;
Goossen, Lukas J.
.
CHEMICAL SCIENCE,
2014, 5 (04)
:1312-1316

Danoun, Gregory
论文数: 0 引用数: 0
h-index: 0
机构:
TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany

Bayarmagnai, Bilguun
论文数: 0 引用数: 0
h-index: 0
机构:
TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany

Gruenberg, Matthias F.
论文数: 0 引用数: 0
h-index: 0
机构:
TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany

Goossen, Lukas J.
论文数: 0 引用数: 0
h-index: 0
机构:
TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany TU Kaiserslautern, FB Chem Organ Chem, D-67663 Kaiserslautern, Germany
[8]
Room temperature palladium-catalyzed 2-arylation of indoles
[J].
Deprez, NR
;
Kalyani, D
;
Krause, A
;
Sanford, MS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (15)
:4972-4973

Deprez, NR
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Kalyani, D
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Krause, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Sanford, MS
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[9]
Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes
[J].
Dubinina, Galyna G.
;
Furutachi, Hideki
;
Vicic, David A.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2008, 130 (27)
:8600-+

Dubinina, Galyna G.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

Furutachi, Hideki
论文数: 0 引用数: 0
h-index: 0
机构:
Kanazawa Univ, Div Mat Sci, Grad Sch Nat Sci & Technol, Kanazawa, Ishikawa 9201192, Japan Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

Vicic, David A.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
[10]
Palladium-Catalyzed Trifluoroethylation of Terminal Alkynes with 1,1,1-Trifluoro-2-iodoethane
[J].
Feng, Yi-Si
;
Xie, Chuan-Qi
;
Qiao, Wen-Long
;
Xu, Hua-Jian
.
ORGANIC LETTERS,
2013, 15 (04)
:936-939

Feng, Yi-Si
论文数: 0 引用数: 0
h-index: 0
机构:
Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China

Xie, Chuan-Qi
论文数: 0 引用数: 0
h-index: 0
机构:
Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China

Qiao, Wen-Long
论文数: 0 引用数: 0
h-index: 0
机构:
Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China

Xu, Hua-Jian
论文数: 0 引用数: 0
h-index: 0
机构:
Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China
Key Lab Adv Funct Mat & Devices, Hefei 230009, Anhui, Peoples R China Hefei Univ Technol, Sch Med Engn, Sch Chem Engn, Hefei 230009, Anhui, Peoples R China