Download PDF
van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/8: C-1 Building Blocks in Organic Synthesis 2 DOI: 10.1055/sos-SD-213-00216
C-1 Building Blocks in Organic Synthesis 2

2.6.1 Trifluoromethylation

More Information

Book

Editor: van Leeuwen, P. W. N. M.

Authors: Ballini, R.; Belderrain, T. R.; Bruneau, C.; Cokoja, M.; Dong, D.; Fischmeister, C.; Grushin, V. V.; Hu, J.; Ibrahim, H.; Iwasawa, N.; Kaposi, M.; Kühn, F. E.; Lishchynskyi, A.; Merino, P.; Molander, G. A.; Müller, C.; MuÇoz-Molina, J. M.; Neumann, H.; Ni, C.; Nicasio, M. C.; Novák, P.; Nozaki, K.; Ouali, A.; Petrini, M.; Rutjes, F. P. J. T.; Ryu, D.; Schoonen, L.; Schranck, J.; Taillefer, M.; Takahashi, K.; Takaya, J.; te Grotenhuis, C.; Witt, J.; Zhang, N.

Title: C-1 Building Blocks in Organic Synthesis 2

Subtitle: Alkenations, Cross Couplings, Insertions, Substitutions, and Halomethylations

Print ISBN: 9783131751218; Online ISBN: 9783132064515; Book DOI: 10.1055/b-003-125817

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: C-1 Building Blocks in Organic Synthesis

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

Also available at
 


Abstract

Metal-catalyzed/-promoted trifluoromethylation reactions represent a powerful tool for the synthesis of a broad variety of organic compounds bearing a CF3 group on sp3-, sp2-, or sp-hybridized carbon atoms.

Key words

trifluoromethylation - fluorine compounds - coupling reactions - copper complexes - copper catalysts - palladium catalysts
 
  • 1 Ma J.-A, Cahard D. J. Fluorine Chem. 2007; 128: 975
  • 2 Ma J.-A, Cahard D. Chem. Rev. 2008; 108: PR1
  • 3 Prakash GKS, Yudin AK. Chem. Rev. 1997; 97: 757
  • 4 Singh RP, Shreeve JM. Tetrahedron 2000; 56: 7613
  • 5 Studer A. Angew. Chem. Int. Ed. 2012; 51: 8950
  • 6 Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
  • 7 Ruppert I, Schlich K, Volbach W. Tetrahedron Lett. 1984; 25: 2195
  • 8 Han W, Li Y, Tang H, Liu H. J. Fluorine Chem. 2012; 140: 7
  • 9 Zanardi A, Novikov MA, Martin E, Benet-Buchholz J, Grushin VV. J. Am. Chem. Soc. 2011; 133: 20901
  • 10 Langlois BR, Billard T. ACS Symp. Ser. 2005; 911: 57
  • 11 Chen Q.-Y, Wu S.-W. J. Chem. Soc., Chem. Commun. 1989; 705
  • 12 Shibata N, Matsnev A, Cahard D. Beilstein J. Org. Chem. 2010; 6: 65
  • 13 Yagupolskii LM, Kondratenko NV, Timofeeva GN. J. Org. Chem. USSR (Engl. Transl.) 1984; 20: 103
  • 14 Umemoto T. Chem. Rev. 1996; 96: 1757
  • 15 Eisenberger P, Gischig S, Togni A. Chem.–Eur. J. 2006; 12: 2579
  • 16 Dolbier Jr WR. Chem. Rev. 1996; 96: 1557
  • 17 Langlois BR, Laurent E, Roidot N. Tetrahedron Lett. 1991; 32: 7525
  • 18 Billard T, Langlois BR. Eur. J. Org. Chem. 2007; 891
  • 19 Shibata N, Mizuta S, Kawai H. Tetrahedron: Asymmetry 2008; 19: 2633
  • 20 Zheng Y, Ma J.-A. Adv. Synth. Catal. 2010; 352: 2745
  • 21 Sato K, Yuki T, Yamaguchi R, Hamano T, Tarui A, Omote M, Kumadaki I, Ando A. J. Org. Chem. 2009; 74: 3815
  • 22 Sato K, Tarui A, Omote M, Ando A, Kumadaki I. Synthesis 2010; 1865
  • 23 Hu M, Ni C, Hu J. J. Am. Chem. Soc. 2012; 134: 15257
  • 24 Novák P, Lishchynskyi A, Grushin VV. J. Am. Chem. Soc. 2012; 134: 16167
  • 25 Herrmann AT, Smith LL, Zakarian A. J. Am. Chem. Soc. 2012; 134: 6976
  • 26 Deng Q.-H, Wadepohl H, Gade LH. J. Am. Chem. Soc. 2012; 134: 10769
  • 27 Allen AE, MacMillan DWC. J. Am. Chem. Soc. 2010; 132: 4986
  • 28 Kitazume T, Ishikawa N. J. Am. Chem. Soc. 1985; 107: 5186
  • 29 Sato K, Omote M, Ando A, Kumadaki I. Org. Lett. 2004; 6: 4359
  • 30 Sato K, Omote M, Ando A, Kumadaki I. Org. Synth., Coll. Vol. XI 2009; 336
  • 31 Mu X, Wu T, Wang H.-Y, Guo Y.-L, Liu G. J. Am. Chem. Soc. 2012; 134: 878
  • 32 Han J, Xu B, Hammond GB. Org. Lett. 2011; 13: 3450
  • 33 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462
  • 34 Janson PG, Ghoneim I, Ilchenko NO, Szabó KJ. Org. Lett. 2012; 14: 2882
  • 35 Matsubara S, Mitani M, Utimoto K. Tetrahedron Lett. 1987; 28: 5857
  • 36 Su D.-B, Duan J.-X, Chen Q.-Y. Tetrahedron Lett. 1991; 32: 7689
  • 37 Chen Q.-Y, Duan J.-X. J. Chem. Soc., Chem. Commun. 1993; 1389
  • 38 Duan J.-X, Su D.-B, Chen Q.-Y. J. Fluorine Chem. 1993; 61: 279
  • 39 Kim J, Shreeve JM. Org. Biomol. Chem. 2004; 2: 2728
  • 40 Tomashenko OA, Escudero-Adán EC, Martínez Belmonte M, Grushin VV. Angew. Chem. Int. Ed. 2011; 50: 7655
  • 41 Zhao TSN, Szabó KJ. Org. Lett. 2012; 14: 3966
  • 42 Chu L, Qing F.-L. Org. Lett. 2012; 14: 2106
  • 43 Miyake Y, Ota S.-i, Nishibayashi Y. Chem.–Eur. J. 2012; 18: 13255
  • 44 Parsons AT, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 9120
  • 45 Shimizu R, Egami H, Hamashima Y, Sodeoka M. Angew. Chem. Int. Ed. 2012; 51: 4577
  • 46 Mizuta S, Galicia-López O, Engle KM, Verhoog S, Wheelhouse K, Rassias G, Gouverneur V. Chem.–Eur. J. 2012; 18: 8583
  • 47 Wang X, Ye Y, Zhang S, Feng J, Xu Y, Zhang Y, Wang J. J. Am. Chem. Soc. 2011; 133: 16410
  • 48 Xu J, Fu Y, Luo D.-F, Jiang Y.-Y, Xiao B, Liu Z.-J, Gong T.-J, Liu L. J. Am. Chem. Soc. 2011; 133: 15300
  • 49 Kobayashi Y, Yamamoto K, Kumadaki I. Tetrahedron Lett. 1979; 20: 4071
  • 50 Kondratenko NV, Vechirko EP, Yagupolskii LM. Synthesis 1980; 932
  • 51 Paratian JM, Labbé E, Sibille S, Périchon J. J. Organomet. Chem. 1995; 489: 137
  • 52 Dubinina GG, Furutachi H, Vicic DA. J. Am. Chem. Soc. 2008; 130: 8600
  • 53 Dubinina GG, Ogikubo J, Vicic DA. Organometallics 2008; 27: 6233
  • 54 Kawai H, Furukawa T, Nomura Y, Tokunaga E, Shibata N. Org. Lett. 2011; 13: 3596
  • 55 Xu J, Xie C.-Q, Luo D.-F, Liu L, Fu Y. Angew. Chem. Int. Ed. 2012; 51: 12551
  • 56 Roy S, Gregg BT, Gribble GW, Le V.-D, Roy S. Tetrahedron 2011; 67: 2161
  • 57 Zhang C.-P, Wang Z.-L, Chen Q.-Y, Zhang C.-T, Gu Y.-C, Xiao J.-C. Angew. Chem. Int. Ed. 2011; 50: 1896
  • 58 Kondo H, Oishi M, Fujikawa K, Amii H. Adv. Synth. Catal. 2011; 353: 1247
  • 59 Popov I, Lindeman S, Daugulis O. J. Am. Chem. Soc. 2011; 133: 9286
  • 60 Li Y, Chen T, Wang H, Zhang R, Jin K, Wang X, Duan C. Synlett 2011; 1713
  • 61 Kremlev MM, Mushta AI, Tyrra W, Yagupolskii YuL, Naumann D, Möller A. J. Fluorine Chem. 2012; 133: 67
  • 62 Morimoto H, Tsubogo T, Litvinas ND, Hartwig JF. Angew. Chem. Int. Ed. 2011; 50: 3793
  • 63 Weng Z, Lee R, Jia W, Yuan Y, Wang W, Feng X, Huang K.-W. Organometallics 2011; 30: 3229
  • 64 Cottet F, Castagnetti E, Schlosser M. Synthesis 2005; 798
  • 65 Cottet F, Schlosser M. Tetrahedron 2004; 60: 11869
  • 66 Cottet F, Schlosser M. Eur. J. Org. Chem. 2004; 3793
  • 67 Oishi M, Kondo H, Amii H. Chem. Commun. (Cambridge) 2009; 1909
  • 68 Inoue M, Araki K, Kawada K. JP 2009 234 921, 2009 Chem. Abstr.. 2009
    Google Scholar
  • 69 Knauber T, Arikan F, Röschenthaler G.-V, Gooßen LJ. Chem.–Eur. J. 2011; 17: 2689
  • 70 Chu L, Qing F.-L. Org. Lett. 2010; 12: 5060
  • 71 Senecal TD, Parsons AT, Buchwald SL. J. Org. Chem. 2011; 76: 1174
  • 72 Khan BA, Buba AE, Gooßen LJ. Chem.–Eur. J. 2012; 18: 1577
  • 73 Litvinas ND, Fier PS, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 536
  • 74 Jiang X, Chu L, Qing F.-L. J. Org. Chem. 2012; 77: 1251
  • 75 Xu J, Luo D.-F, Xiao B, Liu Z.-J, Gong T.-J, Fu Y, Liu L. Chem. Commun. (Cambridge) 2011; 47: 4300
  • 76 Zhang C.-P, Cai J, Zhou C.-B, Wang X.-P, Zheng X, Gu Y.-C, Xiao J.-C. Chem. Commun. (Cambridge) 2011; 47: 9516
  • 77 Liu T, Shen Q. Org. Lett. 2011; 13: 2342
  • 78 Liu T, Shao X, Wu Y, Shen Q. Angew. Chem. Int. Ed. 2012; 51: 540
  • 79 Huang Y, Fang X, Lin X, Li H, He W, Huang K.-W, Yuan Y, Weng Z. Tetrahedron 2012; 68: 9949
  • 80 Ye Y, Sanford MS. J. Am. Chem. Soc. 2012; 134: 9034
  • 81 Ye Y, Kunzi SA, Sanford MS. Org. Lett. 2012; 14: 4979
  • 82 Novák P, Lishchynskyi A, Grushin VV. Angew. Chem. Int. Ed. 2012; 51: 7767
  • 83 Grushin VV, Marshall WJ. J. Am. Chem. Soc. 2006; 128: 4632
  • 84 Grushin VV, Marshall WJ. J. Am. Chem. Soc. 2006; 128: 12644
  • 85 Grushin VV. Acc. Chem. Res. 2010; 43: 160
  • 86 Bakhmutov VI, Bozoglian F, Gómez K, González G, Grushin VV, Macgregor SA, Martin E, Miloserdov FM, Novikov MA, Panetier JA, Romashov LV. Organometallics 2012; 31: 1315
  • 87 Cho EJ, Senecal TD, Kinzel T, Zhang Y, Watson DA, Buchwald SL. Science (Washington, D. C.) 2010; 328: 1679
  • 88 Samant BS, Kabalka GW. Chem. Commun. (Cambridge) 2011; 47: 7236
  • 89 Wiehn MS, Vinogradova EV, Togni A. J. Fluorine Chem. 2010; 131: 951
  • 90 Wang X, Truesdale L, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 3648
  • 91 Zhang X.-G, Dai H.-X, Wasa M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 11948
  • 92 Mu X, Chen S, Zhen X, Liu G. Chem.–Eur. J. 2011; 17: 6039
  • 93 Chu L, Qing F.-L. J. Am. Chem. Soc. 2012; 134: 1298
  • 94 Hafner A, Bräse S. Adv. Synth. Catal. 2011; 353: 3044
  • 95 Nowak I, Robins MJ. J. Org. Chem. 2007; 72: 2678
  • 96 Fei X.-S, Tian W.-S, Chen Q.-Y. J. Chem. Soc., Perkin Trans. 1 1998; 1139
  • 97 Cho EJ, Buchwald SL. Org. Lett. 2011; 13: 6552
  • 98 Parsons AT, Senecal TD, Buchwald SL. Angew. Chem. Int. Ed. 2012; 51: 2947
  • 99 He Z, Luo T, Hu M, Cao Y, Hu J. Angew. Chem. Int. Ed. 2012; 51: 3944
  • 100 Feng C, Loh T.-P. Chem. Sci. 2012; 3: 3458
  • 101 Klyuchinskii SA, Zavgorodnii VS, Lebedev VB, Petrov AA. Zh. Obshch. Khim. 1986; 56: 1663 J. Gen. Chem. USSR (Engl. Transl.) 1986; 56: 1474
  • 102 Chu L, Qing F.-L. J. Am. Chem. Soc. 2010; 132: 7262
  • 103 Zhang K, Qiu X.-L, Huang Y, Qing F.-L. Eur. J. Org. Chem. 2012; 58
  • 104 Luo D.-F, Xu J, Fu Y, Guo Q.-X. Tetrahedron Lett. 2012; 53: 2769
  • 105 Weng Z, Li H, He W, Yao L.-F, Tan J, Chen J, Yuan Y, Huang K.-W. Tetrahedron 2012; 68: 2527