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Organometallics 2014, 33, 5525−5534 - notes. · PDF fileOrganometallics Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII

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  • Organometallics

    Mechanistic Investigations of Cu-Catalyzed Fluorination of Diaryliodonium Salts: Elaborating the CuI/CuIII Manifold in

    CopperCatalysis Naoko Ichiishi, Allan J. Canty, Brian F. Yates, and Melanie S. Sanford,

    Organometallics 2014, 33, 55255534

  • Chemical Communications

    Relay cooperation of K2S2O8 and O2 in oxytrifluoromethylation of alkenes using CF3SO2Na

    Qingquan Lu, Chao Liu, Zhiyuan Huang, Yiyang Ma, Jian Zhanga and Aiwen Lei

    Chem. Commun., 2014, 50, 14101--14104

    K2S2O8(25 mol%)

    450C, DMSO

    X

    R1

    R2

    R1

    O

    CF3

    R2

    CF3SO2Na O2(air)

    Direct CH difluoromethylenephosphonation of arenes and heteroarenes with bromodifluoromethyl phosphonate via visible-light

    photocatalysis Lin Wang, Xiao-Jing Wei, Wen-Long Lei, Han Chen, Li-Zhu Wub and Qiang Liu

    Oxidative tandem nitrosation/cyclization of N-arylenamines with nitromethane toward3-(trifluoromethyl)quinoxalines

    Zhi-Jun Yang, Chuan-Zhuo Liu, Bo-Lun Hu, Chen-Liang Deng and Xing-Guo Zhang

    Chem. Commun., 2014, 50, 1455414557

    HN

    Ph

    CF3

    N

    N CF3

    Ph N

    N CF3

    Ph

    O

    CH3NO2

    CatalistOxidant

    Additive

    HN

    R'

    CF3

    N

    N CF3

    R'

    CH3NO2

    10 mol% KITBHP (2.5 equiv.)

    CsOAc (2.5 equiv.)

    HOAc (2 equiv.)

    1200C, N2

    R R

  • Chem. Commun., 2014, 50, 15916--15919

  • CHEMISTRY An Asian Journal

    Synthesis of Pyridine N-OxideBF2CF3 Complexes and Their FluorescenceProperties

    Tomoaki Nishida, Aiko Fukazawa, Eriko Yamaguchi, Hiroya Oshima, Shigehiro Yamaguchi, Motomu Kanai, and Yoichiro Kuninobu

    Chem. Asian J. 2014, 9, 1026 1030

    New reagent

    BF2CF3 complex with 4-phenylpyridine N-oxide

    K[BF3CF3]

    BF3OEt2(1.1 equiv.)

    CH2Cl2250C, 20 min

    [BF2CF3OEt2]

    N

    Ph

    O

    N

    Ph

    OBF2CF3

    (1.0 equiv.)

    CH2Cl2250C, 1h

    89%

    (1.1 equiv.)

    Stereoselective Nucleophilic Addition of PhSCF2SiMe3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem-Difluoromethylenated

    Polyhydroxypyrrolizidines and-indolizidines Korkit Korvorapun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana

    Tuchinda,Vichai Reutrakul, and Manat Pohmakotr

    Chem. Asian J. 2015, 10, 948 968

  • Organic Letters

    Difluorohomologation of Ketones

    Mikhail D. Kosobokov, Vitalij V. Levin, Marina I. Struchkova, and Alexander D. Dilman Org. Lett. 2015, 17, 760763

    R1

    O

    R3

    R2

    R1

    O

    F F

    R3

    R2

    (a)Mo3SiOTf, NEt3dioxane, rt, 40 min

    (b)Mo3SiCF2Br, HMPA, rt, 3 h

    (c)HBr/AcOH, H2O, 800C, 1 h

  • Journal og Organic Chemistry

    Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from

    Terminal Alkynes JoseRamon Suarez, Daniel Collado-Sanz, Diego J. Cardenas, and Jose Luis Chiara

    J. Org. Chem. 2015, 80, 10981106

    2NfN3(0.6 equiv), DBU(0.6 equiv)

    CuI(2 mol%), CHCl3, rt, 10 minR RR

    Chloro, Difluoromethylation and Chloro, Carbomethoxydifluoromethylation: Reaction of Radicals Derived from

    RfSO2Cl with Unactivated Alkenes under Metal-Free Conditions

    Charles S. Thomoson, Xiao-Jun Tang, and William R. Dolbier, Jr.

    J. Org. Chem. 2015, 80, 12641268

    Cl S

    O

    O

    CF2H R

    Cl

    RCF2H

    DLP(0.4 equv.)

    700C, DCM, 8 h

    O

    MeOS DLP(0.4 equv.)

    700C, DCM, 8 h

    O

    O

    Cl

    F F

    Cl

    O

    MeO

    F F

    Synthesis of Vinyl Trifluoromethyl Thioethers via Copper-

    MediatedTrifluoromethylthiolation of Vinyl Bromides

    Yangjie Huang, Jianping Ding, Chuyi Wu, Huidong Zheng, and Zhiqiang Weng.

    J. Org. Chem. 2015, 80, 29122917

    R

    R1

    Br

    R2

    R

    R1

    SCF3

    R2

    (bpy)Cu(SCF3)

    KF(4 equiv.)Diglime

    1000C, 24 h

    http://pubs.acs.org/action/doSearch?ContribStored=Thomoson%2C+C+Shttp://pubs.acs.org/action/doSearch?ContribStored=Tang%2C+Xhttp://pubs.acs.org/action/doSearch?ContribStored=Dolbier%2C+W+R+Jr.

  • Synthesis of Trifluoromethyl-Containing Vicinal Diamines by Asymmetric Decarboxylative Mannich Addition Reactions

    Lingmin Wu, Chen Xie, Haibo Mei, Yanling Dai, Jianlin Han, Vadim A. Soloshonok,and Yi Pan.

    J. Org. Chem. 2015, 80, 31873194

  • CHEMISTRY A European Journal Communication

    Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides

    Kohsuke Aikawa, Yuzo Nakamura, Yuki Yokota, Wataru Toya, and Koichi Mikami

    Chem. Eur. J. 2015, 21, 96 100

    RI

    RRF

    [A] Zn(C2F5)2(DMPU)2 (1 equiv.)

    CuI (10 mol%)

    DMPU, 900C, 24 h

    [B] Zn(nC6F13)2(DMPU)2 (1 equiv.)

    CuI (10 mol%)

    DMPU, 1200C, 24 h

    Ph

    I

    Ph

    RF

    [A] or [B]

  • Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates

    Dalu Chang, Yang Gu, and Qilong Shen

    Chem. Eur. J. 2015, 21, 6074 6078

    RBr

    [(SIPr)Ag(CF2H)]

    (1.0 equiv.)

    1.0 mol% [Pd}2.0 mol% DPPF

    dioxane

    600C, 24 h

    RCF2H

    [(SIPr)Ag(CF2H)]

    (1.2 equiv.)

    1.0 mol% [Pd}2.0 mol% DPPF

    KBr (2.0 equiv.)

    dioxane

    600C, 24 h

    R

    R'

    OTf/ONf

    R''

    R

    R'

    CF2H

    R''

    [(SIPr)Ag(CF2H)]

    (1.2 equiv.)

    1.0 mol% [Pd}2.0 mol% DPPF

    KBr (2.0 equiv.)

    dioxane

    800C, 24 h

    R

    R'

    OTs

    R''

    R

    R'

    CF2H

    R''

  • European Journal og Organic Chemistry

    Modified Julia Olefination on Sugar-Derived Lactones: Synthesis of Difluoroexo-glycals

    Samuel Habiba] and David Gueyrard

    Eur. J. Org. Chem. 2015, 871875

    Metal-Mediated Reformatsky Reaction of Bromodifluoromethyl Ketone and Imine

    Chun-Ru Cao, Min Jiang, and Jin-Tao Liu

    Eur. J. Org. Chem. 2015, 1144 1151

  • Copper-Catalyzed Innate Ethoxycarbonyldifluoromethylation of Electron-Rich Arenes

    Marie-Charlotte Belhomme, Alexandre Bayle, Thomas Poisson, and Xavier Pannecoucke

    Eur. J. Org. Chem. 2015, 1719 1726

    EDG

    R

    H

    EDG

    R

    CF2COX

    Cu2O (% mol%), L1 (12 mol %)

    K2CO3, BrCF2COX

    DMF, 800C, 16 h

  • Journal of Fluorine Chemistry

    Nucleophilic tetrafluoroethylation of carbonyl compounds with fluorinated sulfones

    Jir Vaclavk , Yana Chernykh, Bronislav Jurasek, Petr Beier

    J. Fluor. Chem. 2015, v.169, pp 2431

    R1 R2

    O

    CF2CF2SO2PhR2

    OH

    R1 PhSO2CF2CF2CF2H

    1. PhSO2CF2CF2SiMe3CsF, DMF, -500C to rt

    2. HCl, H2O, rt

    CF2CF2SO2PhR2

    OH

    R1

    Route A:

    Na, EtOH, THF, rt

    Route B:

    Mg, MeOH, rt

    CF2CF2HR2

    OH

    R1

    General asymmetric synthesis of 2,2,2-trifluoro-1-(1H-indol-3- and -2-yl)ethanamines

    Lingmin Wu, Chen Xie, Jie Zhou, Haibo Mei, Vadim A. Soloshonok, Jianlin Han, Yi Pan

    J. Fluor. Chem. 2015, v.170, pp 5765

    N

    R R

    H

    F3C NS

    O

    N

    R

    R

    H

    NH

    S

    OCF3BF3 EtO2(100 mol %)

    CH2Cl2, 10 h

    -780C to rt

  • Synthesis of (2S,3S)-b-(trifluoromethyl)-a,b-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to N-tert-butylsulfinyl-

    3,3,3-trifluoroacetaldimine

    Akie Kawamura, Hiroki Moriwaki, Gerd-Volker Roschenthaler, Kosuke Kawada, Jose Luis Acena, Vadim A. Soloshonok

    J. Fluor. Chem. 2015, v.171, pp 6772

    F3C NS

    O

    Ph

    Ph

    N CO2R

    (Ss)

    NH

    S

    OCF3

    RO2C

    NPh

    Ph (2S,3S)(Ss)

    F3CCO2H

    NH2

    NH2

    (2S,3S)

    Cs2CO3(10 mol%)

    THF, rt

    89-98%

    Brsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent

    Bingqing Ma, Xinxin Shao, Qilong Shen

    J. Fluor. Chem. 2015, v.171, pp 7377

    N

    R1

    R2ClCH2CH2Cl

    400C, 20-48 h

    Ar

    Me

    Me

    OSCF3N

    R1

    R2

    Ar= 2-iodophenyl

    SCF3

    CSA (10 mol%)

  • Reactions of organozinc reagents with potassium bromodifluoroacetate

    Vitalij V. Levin, Artem A. Zemtsov, Marina I. Struchkova, Alexander D. Dilman

    J. Fluor. Chem. 2015, v.171, pp 97101

    Ph ZnBrrt, 20 h

    Br

    F F

    O

    OK

    Ph

    F F

    ZnBrPh

    F

    F

    AcOH

    DMF, 500C

    Synthesis of tetrafluoroethyl- and tetrafluoroethylene-containing amines by the reaction of silanes with enamines under acidic

    conditions

    Yana Chernykh, Bronislav Jura sek, Petr Beier

    J. Fluor. Chem. 2015, v.171, pp 162168

    DMF, -500C to rtBrCF2CF2Br

    PhSH, NaHPhSCF2CF2Br

    Mg, Me3SiCl

    THF, -780C to rtPhSCF2CF2SiMe3 PhSO2CF2CF2SiMe3

    m-CPBA

    CH2Cl200C to rt

    30% H2O2

    AcOH, 600C

    64%

    90% 92%91%

    S

    O

    N4-Tol Ph

    S

    O

    NH

    *

    Ph

    CF2CF2SPh

    4-TolPhSCF2CF2SiMe3

    OAc (1 equiv.)

    DMF, -400C, 2 h

    20%(2 equiv.)

    dr 83:17

    n-Bu4N

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