Download PDF
Synthesis 2009(23): 3905-3929  
DOI: 10.1055/s-0029-1217080
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Trifluoromethyl Pyrroles and Their Benzo Analogues

Vasiliy M. Muzalevskiya, Aleksey V. Shastinb, Elizabeth S. Balenkovaa, Günter Haufe*c, Valentine G. Nenajdenko*a
a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russian Federation
e-Mail: nen@acylium.chem.msu.ru;
b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russian Federation
e-Mail: shastin@icp.ac.ru;
c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
Further Information

Publication History

Received 9 June 2009
Publication Date:
26 October 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Approaches towards trifluoromethylpyrroles and their benzo analogues are reviewed.

1 Introduction

2 Synthesis of Trifluoromethylpyrroles

2.1 Direct Trifluoromethylation

2.1.1 Radical Trifluoromethylation

2.1.2 Electrophilic Trifluoromethylation

2.1.3 Nucleophilic Trifluoromethylation

2.2 Synthesis by Cycloaddition Reactions

2.2.1 [3+2] Cycloaddition

2.2.2 [4+2] Cycloaddition and Cycloreversion

2.3 Synthesis Based on Carbonyl Compounds

2.4 Synthesis Based on α,β-Unsaturated Trifluoromethyl Ketones

2.5 Synthesis Based on Toluenesulfonylmethyl Isocyanide and Isocyanoacetate

2.6 Miscellaneous Approaches

3 Synthesis of Trifluoromethylindoles

3.1 Direct Trifluoromethylation

3.2 Formation of the C3-C4 Bond

3.3 Formation of the C2-C3 Bond

3.4 Formation of the C2-N Bond

4 Synthesis of Trifluoromethylindolizines

5 Conclusions

Key words

fluorine - heterocycles - pyrroles - indoles

    References

  • 1a Fan H. Peng J. Hamann MT. Hu J.-F. Chem. Rev.  2008,  108:  264 
    Search in Google Scholar
  • 1b Schmuck C. Rupprecht D. Synthesis  2007,  3095 
  • 1c Bellina F. Rossi R. Tetrahedron  2006,  62:  7213 
    Search in Google Scholar
  • 1d Jolicoeur B. Chapman EE. Thompson A. Lubell WD. Tetrahedron  2006,  62:  11531 
    Search in Google Scholar
  • 2a Furin G. Adv. Heterocycl. Chem.  2006,  90:  239 
    Search in Google Scholar
  • 2b Furin G. Adv. Heterocycl. Chem.  2005,  88:  231 
    Search in Google Scholar
  • 2c Furin G. Adv. Heterocycl. Chem.  2004,  87:  273 
    Search in Google Scholar
  • 2d Pace A. Pibiri I. Buscemi S. Vivona N. Heterocycles  2004,  63:  2627 
    Search in Google Scholar
  • 2e Furin G. Adv. Heterocycl. Chem.  2004,  86:  129 
    Search in Google Scholar
  • 2f Zhu SZ. Wang YL. Peng WM. Song LP. Jin GF. Curr. Org. Chem.  2002,  6:  1057 
    Search in Google Scholar
  • 2g Erian AW. J. Heterocycl. Chem.  2001,  38:  793 
    Search in Google Scholar
  • 3a Black BC. Hollingworth RM. Ahammadsahib KI. Kukel CD. Donovan S. Pestic. Biochem. Physiol.  1994,  50:  115 
    Search in Google Scholar
  • 3b Nauen R. Bretschneider T. Pestic. Outlook  2002,  13:  241 
    Search in Google Scholar
  • 3c Dekeyser MA. Pest Manag. Sci.  2005,  61:  103 
    Search in Google Scholar
  • 4 Harriman GCB, Carson KG, Flynn DL, Solomon ME, Song Y, Trivedi BK, Roth BD, Kolz CN, Pham L, and Sun K.-L. inventors; PCT Int. Appl. WO  2002072549. 
  • 5a Baker MT, and Attala MN. inventors; PCT Int. Appl. WO  2003070177. 
  • 5b Akanmu MA. Songkram C. Kagechika H. Honda K. Neurosci. Lett.  2004,  364:  199 
    Search in Google Scholar
  • 6 Romines WH, Kania RS, Lou J, Collins MR, Cripps SJ, He M, Zhou R, Palmer CL, and Deal JG. inventors; PCT Int. Appl. WO  2003106462. 
  • 7a Fukuda Y. Furuta H. Kusama Y. Ebisu H. Oomori Y. Terashima S. J. Med. Chem.  1999,  42:  1448 
    Search in Google Scholar
  • 7b Fukuda Y. Furuta H. Shiga F. Oomori Y. Kusama Y. Ebisu H. Terashima S. Bioorg. Med. Chem. Lett.  1997,  7:  1683 
    Search in Google Scholar
  • 8 Takeo A. Koji K. Masatsugu K. Yoshio S. Junko N. Hisaharu H. Akira S. Bull. Chem. Soc. Jpn.  1988,  61:  3531 
    CrossrefSearch in Google Scholar
  • 9a Masakazu N. Hiroshi K. Shozo F. Yoshio H. Louis C. Bull. Chem. Soc. Jpn.  1991,  64:  2255 
    Search in Google Scholar
  • 9b Kobayashi Y. Kumadaki I. Ohsawa A. Murakami S. Nakano T. Chem. Pharm. Bull.  1978,  26:  1247 
    Search in Google Scholar
  • 10 Girard Y. Atkinson J. Joseph G. Belanger P. Fuentes J. Rokach J. Rooney S. Remy D. Hunt C. J. Org. Chem.  1983,  48:  3220 
    CrossrefSearch in Google Scholar
  • 11 Bovy P. Reitz D. Collins J. Chamberlain T. Olins G. Corpus V. McMahon E. Palomo M. Koepke J. Smits G. McGraw D. Gaw J. J. Med. Chem.  1993,  36:  101 
    CrossrefSearch in Google Scholar
  • 12 Chang MN. Biftu T. Boulton DA. Finke PE. Hammond ML. Pessolano AA. Zambias RA. Bailey P. Goldenberg M. Rackham A. Eur. J. Med. Chem.  1986,  21:  363 
    Search in Google Scholar
  • 13 Chen Q.-Y. Li Z.-T. J. Chem. Soc., Perkin Trans. 1  1993,  645 
    Crossref
  • 14 Yoshida M. Yoshida T. Kobayashi M. Kamigata N. J. Chem. Soc., Perkin Trans. 1  1989,  5:  909 
    CrossrefSearch in Google Scholar
  • 15a Umemoto T. Miyano O. Tetrahedron Lett.  1982,  23:  3929 
    Search in Google Scholar
  • 15b Umemoto T. Miyano O. Toyo Soda Kenkyu Hokoku  1983,  27:  69 ; Chem. Abstr. 1983, 100, 67911
    Search in Google Scholar
  • 16 Naumann D. Kischkewitz J. J. Fluorine Chem.  1990,  46:  265 
    CrossrefSearch in Google Scholar
  • 17a Tordeux M. Langlois B. Wakselman B. J. Chem. Soc., Perkin Trans. 1  1990,  2293 
  • 17b Tordeux M, and Wakselman B. inventors; Eur. Pat. Appl. EP  0298803. 
  • 18 Clavel L, Forat G, Gilbert L, and Nantermet R. inventors; FR  2660923. 
  • 19 Khanna IK. Weier RM. Yu Y. Collins PW. Miyashiro JM. Koboldt CM. Veenhuizen AW. Currie JL. Seibert K. Isakson PC. J. Med. Chem.  1997,  40:  1619 
    CrossrefSearch in Google Scholar
  • 20 Hall A. Atkinson S. Brown SH. Chessell IP. Chowdhury A. Clayton NM. Coleman T. Giblin GMP. Gleave RJ. Hammond B. Healy MP. Johnson MR. Michel AD. Naylor A. Novelli R. Spalding DJ. Tang SP. Bioorg. Med. Chem. Lett.  2006,  16:  3657 
    CrossrefSearch in Google Scholar
  • 21a Langlois BR. Laurent E. Roidot N. Tetrahedron Lett.  1991,  32:  7525 
    Search in Google Scholar
  • 21b Clavel JL, Laurent E, Langlois BR, and Roidot N. inventors; Eur. Pat. Appl. EP  458684. 
  • 22a Umemoto T. Ishihara S. J. Am. Chem. Soc.  1993,  115:  2156 
    Search in Google Scholar
  • 22b Umemoto T. MEC Reagent Brochure   DAIKIN Fine Chemicals Research Center; Tokyo: 1997. 
  • 23a Yang J.-J. Kirchmeier RL. Shreeve JM. J. Org. Chem.  1998,  63:  2656 
    Search in Google Scholar
  • 23b Shreeve JM, Yang J.-J, and Kirchmeier RL. inventors; U.S. Pat. Appl. Publ. US  6215021. 
  • 24 Albaugh PA, Dominguez-Manzanares E, Hong JE, Hornback WJ, Jiang D, Ornstein PL, Thompson ML, Tromiczak EG, Wu Z, Zarrinmayeh H, Zimmerman DM, Castano MAM, Huffman LG, and Miller WD. inventors; PCT Int. Appl. WO  2005040110. 
  • 25 Liu C. Chen Q.-Y. Eur. J. Org. Chem.  2005,  3680 
    Crossref
  • 26 Terazono Y. Dolphin D. J. Org. Chem.  2003,  68:  1892 
    CrossrefSearch in Google Scholar
  • 27 Anderson WK. Corey PF. J. Med. Chem.  1977,  20:  812 
    CrossrefSearch in Google Scholar
  • 28 Padwa A. Burgess EM. Gingrich HL. Roush DM. J. Org. Chem.  1982,  47:  786 
    Search in Google Scholar
  • 29 Meazza G. Bettarini F. La Porta P. Piccardi P. Signorini E. Portoso D. Fornara L. Pest Manag. Sci.  2004,  60:  1178 
    CrossrefSearch in Google Scholar
  • 30 Doehner RF, Barton JM, and Kuhn DG. inventors; U.S. Pat. Appl. Publ. US  5118816. 
  • 31 Huang H. Wu X. Wu N. Huaxue Gongye Yu Gongcheng Jishu  2005,  26:  12 ; Chem. Abstr. 2005, 146, 358652
    Search in Google Scholar
  • 32a Tian W. Luo Y. Chen Y. Yu A. J. Chem. Soc., Chem. Commun.  1993,  101 
  • 32b Wei-Sheng T. Luo Y.-R. Chen Y.-Q. Zai Y.-H. Huaxue Xuebao  1994,  52:  1126 ; Chem. Abstr. 1994, 122, 105575
    Search in Google Scholar
  • 32c Tian W. Chen Y. Luo Y. Deng X. Chin. Chem. Lett.  1991,  2:  217 ; Chem. Abstr. 1991, 115, 114396
    Search in Google Scholar
  • 32d Addor RW, Furch JA, and Kuhn DG. inventors; U.S. Pat. Appl. Publ. US  5030735. 
  • 32e Kagiwara K, Saso H, and Ichinose K. inventors; Jpn. Kokai Tokkyo Koho JP  09301962. 
  • 32f Hagiwara K, Saso H, Ichinose K, Yokota C, and Sano S. inventors; PCT Int. Appl. WO  9617841. 
  • 33a Xu S, Wan Q, Yu Y, Wang X, and Xu Z. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1439634. 
  • 33b Lai H. Mu J. Zeng Q. Li W. Zhejiang Gongye Daxue Xuebao  2003,  31:  692 ; Chem. Abstr. 2003, 141, 243267
    Search in Google Scholar
  • 33c Xu S. Jiang M. Yu Y. Wang X. Wan Q. Xu Z. Nanjing Nongye Daxue Xuebao  2004,  27:  105 ; Chem. Abstr. 2004, 144, 173068
    Search in Google Scholar
  • 34 Tian W. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1140713. 
  • 35 Kuhn DG, Furch JA, and Kamhi VM. inventors; Eur. Pat. Appl. EP  0487870. 
  • 36 Steglich W. Gruber P. Heininger HU. Kneidl F. Chem. Ber.  1971,  104:  3816 
    CrossrefSearch in Google Scholar
  • 37a Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5945538. 
  • 37b Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5777132. 
  • 37c Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5750726. 
  • 37d Kameswaran V. inventors; Eur. Pat. Appl. EP  816337. 
  • 37e Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5925773. 
  • 38a Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5631379. 
  • 38b Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5446170. 
  • 39 Funabiki K. Ishihara T. Yamanaka H. J. Fluorine Chem.  1995,  71:  5 
    CrossrefSearch in Google Scholar
  • 40 Uhr H, Lui N, Erdelen C, and Turberg A. inventors; Ger. Offen. DE  4325132. 
  • 41 Okano T. Uekawa T. Morishima N. Eguchi S. J. Org. Chem.  1991,  56:  5259 
    CrossrefSearch in Google Scholar
  • 42 Tanaka K. Nagatani S. Ohsuga M. Mitshuhashi K. Bull. Chem. Soc. Jpn.  1994,  67:  589 
    CrossrefSearch in Google Scholar
  • 43 Leroy J. Wakselman TC. Can. J. Chem.  1976,  54:  218 
    CrossrefSearch in Google Scholar
  • 44 Leroy J. Cantacuzene D. Wakselman C. Synthesis  1982,  313 
    Thieme Connect
  • 45 La Porta P. Capuzzi L. Bettarini F. Synthesis  1994,  287 
    Thieme Connect
  • 46a Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5965773. 
  • 46b Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  5817834. 
  • 47a Kameswaran V. inventors; U.S. Pat. Appl. Publ. US  6034273. 
  • 47b Kameswaran V. inventors; Eur. Pat. Appl. EP  0934929. 
  • 48a Kameswaran V. inventors; Eur. Pat. Appl. EP  1035113. 
  • 48b Duerr D, Ehrenfreund J, Hall RG, and Danko P. inventors; PCT Int. Appl. WO  9518122. 
  • 49 Potts KT. Choudhury DR. J. Org. Chem.  1978,  43:  2697 
    CrossrefSearch in Google Scholar
  • 50 Zhang X.-C. Huang W.-Y. Tetrahedron  1998,  54:  12465 
    CrossrefSearch in Google Scholar
  • 51 Murray WV. Francois D. Maden A. Turchi I. J. Org. Chem.  2007,  72:  3097 
    CrossrefPubMedSearch in Google Scholar
  • 52 Kobayashi Y. Ando A. Kawada K. Ohsawa A. Kumadaki I. J. Org. Chem.  1980,  45:  2962 
    CrossrefSearch in Google Scholar
  • 53 Kobayashi Y. Ando A. Kawada K. Kumadaki I. J. Org. Chem.  1980,  45:  2968 
    CrossrefSearch in Google Scholar
  • 54 Moiseev SV. Vasil’ev NV. Russ. Chem. Bull.  2005,  54:  1948 
    CrossrefSearch in Google Scholar
  • 55 Kaesler RW. LeGoff E. J. Org. Chem.  1982,  47:  4779 
    CrossrefSearch in Google Scholar
  • 56 Visnick M. Battiste MA. J. Chem. Soc., Chem. Commun.  1985,  1621 
    Crossref
  • 57 Roth BD. Ortwine DF. Hoefle ML. Stratton CD. Sliskovic DR. Wilson MW. Newton RS. J. Med. Chem.  1990,  33:  21 
    CrossrefSearch in Google Scholar
  • 58 Nagarajan K. Talwalker PK. Goud AN. Shah RK. Shenoy SJ. Desai ND. Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1988,  27:  1113 
    Search in Google Scholar
  • 59 Xu G. Singh MP. Gopal D. Sayre LM. Chem. Res. Toxicol.  2001,  14:  264 
    CrossrefSearch in Google Scholar
  • 60 Hoffmann MG. Wenkert E. Tetrahedron  1993,  49:  1057 
    CrossrefSearch in Google Scholar
  • 61 Bouillon J.-P. Henin B. Huot J.-F. Portella C. Eur. J. Org. Chem.  2002,  1556 
    Crossref
  • 62 Jones RA. Rustidge DC. Cushman SM. Synth. Commun.  1984,  14:  575 
    CrossrefSearch in Google Scholar
  • 63a Ogoshi H. Homma M. Yokota K. Toi H. Aoyama Y. Tetrahedron Lett.  1983,  24:  929 
    Search in Google Scholar
  • 63b inventors; Jpn. Kokai Tokkyo Koho JP  59167568. Central Glass Co. Ltd. Japan;
  • 64 Ward RW, and Goudie AC. inventors; Brit. UK Pat. Appl. GB  2107304. 
  • 65 Iwata S. Ishiguro Y. Itsugi M. Mitsuhashi K. Tanaka K. Bull. Chem. Soc. Jpn.  1993,  66:  2432 
    CrossrefSearch in Google Scholar
  • 66 Tessier J, Demoute JP, and Taliani L. inventors; Eur. Pat. Appl. EP  176387. 
  • 67a Kameswaran V. Jiang B. Synthesis  1997,  530 
  • 67b Kameswaran V. inventors; Eur. Pat. Appl. EP  0491137. 
  • 68 Baxter AJG. Fuher J. Teague SJ. Synthesis  1994,  207 
    Thieme Connect
  • 69 Attanasi OA. Filippone P. Guidi B. Mantellini F. Santeusanio S. Synthesis  2001,  1837 
    Thieme Connect
  • 70 Baraznenok IL. Nenajdenko VG. Balenkova ES. Tetrahedron  2000,  56:  3077 
    CrossrefSearch in Google Scholar
  • 71 Shi D. Dou G. Shi C. Li Z. Ji S.-J. Synthesis  2007,  3117 
    Thieme Connect
  • 72 Kathriarachchi KKADS. Siriwardana AI. Nakamura I. Yamamoto Y. Tetrahedron Lett.  2007,  48:  2267 
    CrossrefSearch in Google Scholar
  • 73 Shindo M. Yoshimura Y. Hayashi M. Soejima H. Yoshikawa T. Matsumoto K. Shishido K. Org. Lett.  2007,  9:  1963 
    CrossrefSearch in Google Scholar
  • 74 Ohkura H. Berbasov DO. Soloshonok VA. Tetrahedron Lett.  2003,  44:  2417 
    CrossrefSearch in Google Scholar
  • 75 Klappa JJ. Rich AE. McNeill K. Org. Lett.  2002,  4:  435 
    CrossrefSearch in Google Scholar
  • 76a Nenajdenko VG. Sanin AV. Balenkova ES. Molecules  1997,  2:  186 
    Search in Google Scholar
  • 76b Nenaidenko VG. Sanin AV. Balenkova ES. Russ. Chem. Rev.  1999,  68:  437 
    Search in Google Scholar
  • 76c Druzhinin SV. Balenkova ES. Nenajdenko VG. Tetrahedron  2007,  63:  7753 
    Search in Google Scholar
  • 77 Okada E. Masuda R. Hojo M. Inoue R. Synthesis  1992,  533 
    Thieme Connect
  • 78 Soufyane M. Mirand C. Lévy J. Tetrahedron Lett.  1993,  34:  7737 
    CrossrefSearch in Google Scholar
  • 79 Andrew RJ. Mellor JM. Tetrahedron  2000,  56:  7267 
    CrossrefSearch in Google Scholar
  • 80 Shaitanova EN. Gerus II. Kukhar VP. Tetrahedron Lett.  2008,  49:  1184 
    CrossrefSearch in Google Scholar
  • 81 Bartnik R. Bensadat A. Cal D. Faure R. Khatimi N. Laurent A. Laurent E. Rizzon C. Bull. Soc. Chim. Fr.  1997,  134:  725 
    Search in Google Scholar
  • 82 Cebulska Z. Laurent AJ. Laurent EG. Bull. Soc. Chim. Fr.  1996,  133:  209 
    Search in Google Scholar
  • 83 Zanatta N. Schneider JM. Schneider PH. Wouters AD. Bonacorso HG. Martins MAP. Wessjohann LA. J. Org. Chem.  2006,  71:  6996 
    CrossrefPubMedSearch in Google Scholar
  • 84 Uno H. Tanaka M. Inoue T. Ono N. Synthesis  1999,  471 
    Thieme Connect
  • 85 Larionov OV. de Meijere A. Angew. Chem.  2005,  117:  5809 ; Angew. Chem. Int. Ed. 2005, 44, 5664
    CrossrefSearch in Google Scholar
  • 86a Aoyagi K. Toi H. Aoyama Y. Ogoshi H. Chem. Lett.  1988,  1891 
  • 86b Aoyagi K. Haga T. Toi H. Aoyama Y. Mizutani T. Ogoshi H. Bull. Chem. Soc. Jpn.  1997,  70:  937 
    Search in Google Scholar
  • 87 Leroy J. J. Fluorine Chem.  1991,  53:  61 
    CrossrefSearch in Google Scholar
  • 88 Ono N. Kawamura H. Maruyama K. Bull. Chem. Soc. Jpn.  1989,  62:  3386 
    CrossrefSearch in Google Scholar
  • 89a Tang J. Verkade JG. J. Org. Chem.  1994,  59:  7793 
    Search in Google Scholar
  • 89b Verkade J, and Tang J. inventors; U.S. Pat. Appl. Publ. US  5367084. 
  • 90 Briscoe MW. Chambers RD. Mullins SJ. Nakamura T. Drakesmith FG. J. Chem. Soc., Chem. Commun.  1990,  1127 
    Crossref
  • 91 Chambers RD. Gray WK. Mullins SJ. Korn SR. J. Chem. Soc., Perkin Trans. 1  1997,  1457 
  • 92a Lee LF. Howe RK. J. Org. Chem.  1984,  49:  4780 
    Search in Google Scholar
  • 92b Howe R. inventors; Eur. Pat. Appl. EP  0088743. 
  • 93 Foster R. Gilchrist TL. J. Chem. Soc., Perkin Trans. 1  1991,  2249 
    Crossref
  • 94 Jacobson MA. Willard PG. J. Org. Chem.  2002,  67:  32 
    CrossrefSearch in Google Scholar
  • 95 Roskamp EJ. Dragovich PS. Hartung JB. Pedersen SF. J. Org. Chem.  1989,  54:  4736 
    CrossrefSearch in Google Scholar
  • 96 Zimmer R. Reissig H. J. Org. Chem.  1992,  57:  339 
    CrossrefSearch in Google Scholar
  • 97 Koshelev VM. Truskanova TD. Chekhlov NV. Vasil’ev NV. Gontar’ AF. Russ. Chem. Bull.  1989,  38:  1325 
    CrossrefSearch in Google Scholar
  • 98 Lu L. Chen G. Ma S. Org. Lett.  2006,  8:  835 
    CrossrefSearch in Google Scholar
  • 99 Katritzky AR. Huang T.-B. Voronkov MV. Wang MG. Kolb H. J. Org. Chem.  2000,  65:  8819 
    CrossrefPubMedSearch in Google Scholar
  • 100 Kawase M. Miyamae H. Saito S. Heterocycles  1999,  50:  71 
    CrossrefSearch in Google Scholar
  • 101 Qiu X.-L. Qing F.-L. J. Org. Chem.  2003,  68:  3614 
    CrossrefSearch in Google Scholar
  • 102 De Matteis V. Dufay O. Waalboer DCJ. Van Delft FL. Tiebes J. Rutjes FPJT. Eur. J. Org. Chem.  2007,  2667 
    Crossref
  • 103 Henegar KE. Hunt DA. Heterocycles  1996,  42:  1471 
    Search in Google Scholar
  • 104a Kobayashi Y. Kumadaki I. Ohsawa A. Hamana H. Tetrahedron Lett.  1977,  18:  867 
    Search in Google Scholar
  • 104b Kobayashi Y. Hamana H. Fujino S. Ohsawa A. Kumadaki I. J. Org. Chem.  1979,  44:  4930 
    Search in Google Scholar
  • 105 Dan-oh Y. Matta H. Uemura J. Watanabe H. Uneyama K. Bull. Chem. Soc. Jpn.  1995,  68:  1497 
    CrossrefSearch in Google Scholar
  • 106 Ueda Y. Watanabe H. Uemura J. Uneyama K. Tetrahedron Lett.  1993,  34:  7933 
    CrossrefSearch in Google Scholar
  • 107a Latham EJ. Stanforth SP. Chem. Commun.  1996,  2253 
  • 107b Latham EJ. Stanforth SP. J. Chem. Soc., Perkin Trans. 1  1997,  2059 
  • 108a Chae J. Konno T. Ishihara T. Yamanaka H. Chem. Lett.  2004,  33:  314 
    Search in Google Scholar
  • 108b Konno T. Chae J. Ishihara T. Yamanaka H. J. Org. Chem.  2004,  69:  8258 
    Search in Google Scholar
  • 109 Rodrigues I. Bonnet-Delpon D. Begue J.-P. J. Org. Chem.  2001,  66:  2098 
    CrossrefPubMedSearch in Google Scholar
  • 110a Muzalevskiy VM. Nenajdenko VG. Shastin AV. Balenkova ES. Haufe G. Tetrahedron  2009,  65:  7553 
    Search in Google Scholar
  • 110b For synthesis of enamines 305 see: Muzalevskiy VM. Nenajdenko VG. Shastin AV. Balenkova ES. Haufe G. Tetrahedron  2009,  65:  6991 
    Search in Google Scholar
  • 111 Orlemans EOM. Schreuder AH. Conti PGM. Verboom W. Reinhoudt DN. Tetrahedron  1987,  43:  3817 
    CrossrefSearch in Google Scholar
  • 112a Miyashita K. Kondoh K. Tsuchiya K. Miyabe H. Imanishi T. J. Chem. Soc., Perkin Trans. 1  1996,  1261 
  • 112b Miyashita K. Tsuchiya K. Kondoh K. Miyabe H. Imanishi T. Heterocycles  1996,  42:  513 
    Search in Google Scholar
  • 113a Betschmann P, Burchat AF, Calderwood DJ, Curtin ML, Davidsen SK, Davis HM, Frey RR, Heyman HR, Hirst GC, Hrnciar P, Michaelides MR, Muckey MA, Rafferty P, and Wada CK. inventors; U.S. Pat. Appl. Publ. US  2005043347. 
  • 113b Betschmann P, Burchat AF, Calderwood DJ, Curtin ML, Davidsen SK, Davis HM, Frey RR, Heyman HR, Hirst GC, Hrnciar P, Michaelides MR, Muckey MA, Rafferty P, and Wada CK. inventors; U.S. Pat. Appl. Publ. US  2005026944. 
  • 114a Hojo M. Masuda R. Okada E. Miya H. Synthesis  1989,  550 
  • 114b Okada E. Tsukushi N. Synlett  1999,  210 
  • 114c Okada E. Tsukushi N. Heterocycles  2000,  53:  127 
    Search in Google Scholar
  • 115a Fuerstner A. Hupperts A. Ptock A. Janssen E. J. Org. Chem.  1994,  59:  5215 
    Search in Google Scholar
  • 115b Fuerstner A. Hupperts A. J. Am. Chem. Soc.  1995,  117:  4468 
    Search in Google Scholar
  • 116a Frey LF. Tillyer RD. Ouellet SG. Reamer RA. Grabowski EJJ. Reider PJ. J. Am. Chem. Soc.  2000,  122:  1215 
    Search in Google Scholar
  • 116b Frey LF, Grabowski EJJ, Ouellet SG, Reamer RA, and Tillyer RD. inventors; Brit. UK Pat. Appl. GB  2353035. 
  • 117a Hao J, and Song X. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1660806. 
  • 117b Hao J, Ge F, Wang Z, and Wan W. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1844098. 
  • 117c Hao J, Ge F, Wang Z, and Wan W. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1869022. 
  • 117d Hao J, Wang Z, and Ge F. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  1927834. 
  • 117e Ge F. Wang Z. Wan W. Hao J. Synlett  2007,  447 
  • 117f Wang Z. Ge F. Wan W. Jiang H. Hao J. J. Fluorine Chem.  2007,  128:  1143 
    Search in Google Scholar
  • 118 Fang Y.-Q. Lautens M. Org. Lett.  2005,  7:  3549 
    CrossrefPubMedSearch in Google Scholar
  • 119 Yamakawa A, and Horino Y. inventors; Jpn. Kokai Tokkyo Koho JP  2008037760. 
  • 120a Mokrushin MG. Shastin AV. Muzalevskiy VM. Balenkova ES. Nenajdenko VG. Mendeleev Commun.  2008,  18:  327 
    Search in Google Scholar
  • β-Halogen-β-(trifluoromethyl)styrenes are easily avalaible by the catalytic olefination reaction. For key publications see:
  • 120b Shastin AV. Korotchenko VN. Nenajdenko VG. Balenkova ES. Tetrahedron  2000,  56:  6557 
    Search in Google Scholar
  • 120c Korotchenko VN. Shastin AV. Nenajdenko VG. Balenkova ES. Synthesis  2001,  2081 
  • 120d Korotchenko VN. Shastin AV. Nenajdenko VG. Balenkova ES. J. Chem. Soc. Perkin Trans. 1  2002,  883 
  • 120e Korotchenko VN. Nenajdenko VG. Shastin AV. Balenkova ES. Org. Biomol. Chem.  2003,  1906 
  • 120f Nenajdenko VG. Shastin AV. Korotchenko VN. Varseev GN. Balenkova ES. Eur. J. Org. Chem.  2003,  302 
  • 120g Nenajdenko VG. Varseev GN. Korotchenko VN. Shastin AV. Balenkova ES. J. Fluorine Chem.  2004,  125:  1339 
    Search in Google Scholar
  • 120h Nenajdenko VG. Varseev GN. Shastin AV. Balenkova ES. J. Fluorine Chem.  2005,  126:  907 
    Search in Google Scholar
  • 121 Muzalevskiy VM. Shastin AV. Balenkova ES. Haufe G. Nenajdenko VG. Izv. Akad. Nauk Ser. Khim.  2008,  2177 ; Russ. Chem. Bull. 2008, 2217
  • 122 Chen Y. Wang Y. Sun Z. Ma D. Org. Lett.  2008,  10:  625 
    CrossrefSearch in Google Scholar
  • 123 Kutsuma T. Fujiyama K. Sekine Y. Kobayashi Y. Chem. Pharm. Bull.  1972,  1558 
  • 124a Banks RE. Hitchen SM. Thomson J. J. Fluorine Chem.  1982,  20:  127 
    Search in Google Scholar
  • 124b Banks RE. Thomson J. J. Chem. Res., Synop.  1985,  33 
  • 124c Banks RE. Mohialdin SN. J. Fluorine Chem.  1986,  34:  275 
    Search in Google Scholar
  • 124d Banks RE. Mohialdin SN. J. Fluorine Chem.  1988,  38:  289 
    Search in Google Scholar
  • 124e Banks RE. Khaffaff SN. J. Fluorine Chem.  1991,  51:  407 
    Search in Google Scholar
  • 125a Wu K. Chen Q.-Y. Synthesis  2003,  35 
  • 125b Zhang X.-C. Huang W.-Y. Synthesis  1999,  51 
  • 126 Zhang X.-C. Huang W.-Y. J. Fluorine Chem.  1998,  87:  57 
    CrossrefSearch in Google Scholar
  • 127 Shen Y. Zhang Y. Jiang G.-F. Synthesis  2002,  714 
    Thieme Connect
  • 128 Shen Y. Zhang Y. Sun J. J. Fluorine Chem.  2002,  116:  157 
    CrossrefSearch in Google Scholar
  • 129 Xiao J.-C. Chen Q.-Y. Chin. J. Chem.  2003,  21:  898 
    Search in Google Scholar
  • 130 Xie Y, Holmqvist M, Mahiou J, Ono M, Sun L, Chen S, Zhang S, and Jiang J. inventors; PCT Int. Appl. WO  009954.