FeF3/I2-Catalyzed
Synthesis of 4-Chalcogen-Substituted Arylamines by Direct Thiolation
of an Arene C-H Bond

Xiao-Li Fang; Ri-Yuan Tang; Xing-Guo Zhang; Jin-Heng Li

doi:10.1055/s-0030-1258449

PAPER

FeF₃/I₂-Catalyzed Synthesis of 4-Chalcogen-Substituted Arylamines by Direct Thiolation of an Arene C-H Bond

Xiao-Li Fang^a, Ri-Yuan Tang^a, Xing-Guo Zhang*^a, Jin-Heng Li*^a,b
^a College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
^b Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)88872576; e-Mail: jhli@hunnu.edu.cn;

Abstract

All articles of this category

Abstract

An efficient regioselective synthesis of 4-chalcogen-substituted arylamines by FeF₃-catalyzed sulfenylation and selenation of arylamines has been developed. In the presence of FeF₃and I₂, a variety of arylamines underwent the reaction with disulfides or diselenides to afford the corresponding 4-sulfenyl- or 4-selenenylarylamines in moderate to good yields.

Key words

iron - iodine - sulfenylation - selenation - arylamine - 4-chalcogen-substituted arylamine

Full Text

References

<A NAME="RH58110SS-1A">1a</A> Liu G. Huth JR. Olejniczak ET. Mendoza R. DeVries P. Leitza S. Reilly EB. Okasinski GF. Fesik SW. von Geldern TW. J. Med. Chem. 2001, 44: 1202

<A NAME="RH58110SS-1B">1b</A> De Martino G. Edler MC. La Regina G. Coluccia A. Barbera MC. Barrow D. Nicholson RI. Chiosis G. Brancale A. Hamel E. Artico M. Silvestri R. J. Med. Chem. 2006, 49: 947

<A NAME="RH58110SS-1C">1c</A> Nose M. Suzuki H. Synthesis 2002, 1065

<A NAME="RH58110SS-2A">2a</A> Sousa SCA. Fernandes AC. Tetrahedron Lett. 2009, 50: 6872

<A NAME="RH58110SS-2B">2b</A> Khurana JM. Sharma V. Chako SA. Tetrahedron 2007, 63: 966

<A NAME="RH58110SS-2C">2c</A> Bahrami K. Khodaei MM. Karimi A. Synthesis 2008, 2543

For reviews, see:

<A NAME="RH58110SS-3A">3a</A> Kondo T. Mitsudo T. Chem. Rev. 2000, 100: 3205

<A NAME="RH58110SS-3B">3b</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RH58110SS-3C">3c</A> Hartwig JF. Acc. Chem. Res. 2008, 41: 1534

<A NAME="RH58110SS-3D">3d</A> Kunz K. Scholz U. Ganzer D. Synlett 2003, 2428

For selected papers on Pd-catalyzed C-S coupling reactions, see:

<A NAME="RH58110SS-4A">4a</A> Fernández-Rodriguez MA. Hartwig JF. J. Org. Chem. 2009, 74: 1663

<A NAME="RH58110SS-4B">4b</A> Murata M. Buchwald SL. Tetrahedron 2004, 60: 7397

<A NAME="RH58110SS-4C">4c</A> Schopfer U. Schlapbach A. Tetrahedron 2001, 57: 3069

<A NAME="RH58110SS-4D">4d</A> Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513

<A NAME="RH58110SS-4E">4e</A> Moreau X. Campagne JM. Meyer G. Jutand A. Eur. J. Org. Chem. 2005, 3749

<A NAME="RH58110SS-4F">4f</A> Li GY. Zheng G. Noonan AF. J. Org. Chem. 2001, 66: 8677

For selected papers on copper-catalyzed C-S coupling reactions, see:

<A NAME="RH58110SS-5A">5a</A> Kabir MS. Lorenz M. Van Linn ML. Namjoshi OA. Ara S. Cook JM. J. Org. Chem. 2010, 75: 3626

<A NAME="RH58110SS-5B">5b</A> Kwong FY. Buchwald SL. Org. Lett. 2002, 4: 3517

<A NAME="RH58110SS-5C">5c</A> Wu Y.-J. He H. Synlett 2003, 1789

<A NAME="RH58110SS-5D">5d</A> Chen Y.-J. Chen H.-H. Org. Lett. 2006, 8: 5609

<A NAME="RH58110SS-5E">5e</A> Zhu D. Xu L. Wu F. Wan BS. Tetrahedron Lett. 2006, 47: 5781

<A NAME="RH58110SS-5F">5f</A> Herrero MT. San Martin R. Domínguez E. Tetrahedron 2009, 65: 1500

<A NAME="RH58110SS-5G">5g</A> Buranaprasertsuk P. Chang JWW. Chavasiri W. Chan PWH. Tetrahedron Lett. 2008, 49: 2023

<A NAME="RH58110SS-5H">5h</A> Lv X. Bao W. J. Org. Chem. 2007, 72: 3863

<A NAME="RH58110SS-6A">6a</A> Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem. 2009, 74: 1971

<A NAME="RH58110SS-6B">6b</A> Fernandez Rodríguez MA. Shen Q. Hartwig JF. J. Am. Chem. Soc. 2006, 128: 2180

<A NAME="RH58110SS-6C">6c</A> Mispelaere-Canivet C. Spindler J.-F. Perrio S. Beslin P. Tetrahedron 2005, 61: 5253

<A NAME="RH58110SS-6D">6d</A> Itoh T. Mase T. Org. Lett. 2004, 6: 4587

<A NAME="RH58110SS-6E">6e</A> Zheng N. McWilliams JC. Fleitz FJ. Armstrong JD. Volante RP. J. Org. Chem. 1998, 63: 9606

<A NAME="RH58110SS-7A">7a</A> Eichman CC. Stambuli JP. J. Org. Chem. 2009, 74: 4005

<A NAME="RH58110SS-7B">7b</A> Correa A. Carril M. Bolm C. Angew. Chem. Int. Ed. 2008, 47: 2880

<A NAME="RH58110SS-7C">7c</A> Reddy VP. Kumar AV. Swapna K. Rao KR. Org. Lett. 2009, 11: 1697

<A NAME="RH58110SS-7D">7d</A> Nakamura I. Sato T. Yamamoto Y. Angew. Chem. Int. Ed. 2006, 45: 4473

<A NAME="RH58110SS-8A">8a</A> Taniguchi N. J. Org. Chem. 2007, 72: 1241

<A NAME="RH58110SS-8B">8b</A> Taniguchi N. J. Org. Chem. 2004, 69: 6904

<A NAME="RH58110SS-8C">8c</A> Taniguchi N. Onami T. Synlett 2003, 829

<A NAME="RH58110SS-8D">8d</A> Taniguchi N. Onami T. J. Org. Chem. 2004, 69: 915

<A NAME="RH58110SS-8E">8e</A> G ómez-Benítez V. Baldovino-Pantaleón O. Herrera-Álvarez C. Toscano RA. Morales-Morales D. Tetrahedron Lett. 2006, 47: 5059

<A NAME="RH58110SS-8F">8f</A> Kumar S. Engman L. J. Org. Chem. 2006, 71: 5400

<A NAME="RH58110SS-8G">8g</A> Baldovino-Pantaleón O. Hernandez-Ortega S. Morales-Morales D. Adv. Synth. Catal. 2006, 348: 236

<A NAME="RH58110SS-8H">8h</A> Fukuzawa S.-i. Tanihara D. Kikuchi S. Synlett 2006, 2145

<A NAME="RH58110SS-8I">8i</A> Takeuchi H. Hiyama T. Kamai N. Oya H. J. Chem. Soc., Perkin Trans. 2 1997, 2301

<A NAME="RH58110SS-8J">8j</A> Takeuchi H. Suga K. J. Chem. Soc., Perkin Trans. 2 2000, 1803

For selected recent reviews, see:

<A NAME="RH58110SS-9A">9a</A> Dyker G. Handbook of C-H Transformations. Applications in Organic Synthesis Wiley-VCH; Weinheim: 2005.

<A NAME="RH58110SS-9B">9b</A> Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010, 110: 624

<A NAME="RH58110SS-9C">9c</A> Lyons TW. Sanford MS. Chem. Rev. 2010, 110: 1147

<A NAME="RH58110SS-9D">9d</A> Mkhalid IA. Barnard JH. Marder TB. Murphy JM. Hartwig JF. Chem. Rev. 2010, 110: 890

<A NAME="RH58110SS-9E">9e</A> Zhang M. Adv. Synth. Catal. 2009, 351: 2243

<A NAME="RH58110SS-9F">9f</A> Mori A. Sugie A. Bull. Chem. Soc. Jpn. 2008, 81: 548

<A NAME="RH58110SS-9G">9g</A> Diaz-Requejo MM. Pérez PJ. Chem. Rev. 2008, 108: 3379

<A NAME="RH58110SS-10A">10a</A> Chu L. Yue X. Qing F.-L. Org. Lett. 2010, 12: 1644

<A NAME="RH58110SS-10B">10b</A> Zhao X. Dimitrijevic E. Dong VM. J. Am. Chem. Soc. 2009, 131: 3466

<A NAME="RH58110SS-10C">10c</A> Fukuzawa S.-i. Shimizu E. Atsuumi Y. Haga M. Ogata K. Tetrahedron Lett. 2009, 50: 2374

<A NAME="RH58110SS-10D">10d</A> Joyce LL. Batey RA. Org. Lett. 2009, 11: 2792

<A NAME="RH58110SS-10E">10e</A> Inamoto K. Hasegawa C. Hiroya K. Doi T. Org. Lett. 2008, 10: 5147

<A NAME="RH58110SS-10F">10f</A> Chen X. Hao X.-S. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc. 2006, 128: 6790

<A NAME="RH58110SS-10G">10g</A> Ranken PF. McKinnie GB. J. Org. Chem. 1989, 54: 2985

<A NAME="RH58110SS-11">11</A> Yadav JS. Reddy BVS. Reddy YJ. Praneeth K. Synthesis 2009, 1520

<A NAME="RH58110SS-12">12</A> Fang XL. Tang RY. Zhong P. Li JH. Synthesis 2009, 4183

<A NAME="RH58110SS-13A">13a</A> Tang R.-Y. Zhong P. Lin Q.-L. J. Fluorine Chem. 2006, 127: 948

<A NAME="RH58110SS-13B">13b</A> Tang R.-Y. Zhong P. Lin Q.-L. Synlett 2007, 85

<A NAME="RH58110SS-13C">13c</A> Wang Z.-L. Tang R.-Y. Luo P.-S. Deng C.-L. Zhong P. Li J.-H. Tetrahedron 2008, 64: 10670

<A NAME="RH58110SS-13D">13d</A> Luo P.-S. Yu M. Tang R.-Y. Zhong P.
Li J.-H. Tetrahedron Lett. 2009, 50: 1066

<A NAME="RH58110SS-13E">13e</A> Luo P.-S. Wang F. Li J.-H. Tang R.-Y. Zhong P. Synthesis 2009, 921

<A NAME="RH58110SS-13F">13f</A> Guo Y.-J. Tang R.-Y. Li J.-H. Zhong P. Zhang X.-G. Adv. Catal. Synth. 2009, 351: 2615

<A NAME="RH58110SS-14A">14a</A> Waterson AG. Petrov KG. Hornberger KR. Hubbard RD. Sammond DM. Smith SC. Dickson HD. Caferro TR. Hinkle KW. Stevens KL. Dickerson SH. Rusnak DW. Spehar GM. Wood ER. Griffin RJ. Uehling DE. Bioorg. Med. Chem. Lett. 2009, 19: 1332

<A NAME="RH58110SS-14B">14b</A> Seto M. Miyamoto N. Aikawa K. Aramaki Y. Kanzaki N. Iizawa Y. Baba M. Shiraishi M. Bioorg. Med. Chem. 2004, 13: 363

<A NAME="RH58110SS-14C">14c</A> Delarge J. Thunus L. Beckers C. Ghys A. Denef J. Jamoulle JC. Eur. J. Med. Chem. 1984, 19: 559

<A NAME="RH58110SS-15">15</A> Fujisawa T. Kojima T. J. Org. Chem. 1973, 38: 687

<A NAME="RH58110SS-16">16</A> Wong Y.-C. Jayanth TT. Cheng C.-C. Org. Lett. 2006, 8: 5613

<A NAME="RH58110SS-17">17</A> Marcincal-Lefebvre A. J. Med. Chem. 1981, 24: 889

<A NAME="RH58110SS-18">18</A> Zhang Y. Org. Lett. 2007, 9: 3495

<A NAME="RH58110SS-19">19</A> Moore ML. J. Am. Chem. Soc. 1935, 57: 1517

<A NAME="RH58110SS-20">20</A> Selva M. J. Org. Chem. 2005, 70: 2476

<A NAME="RH58110SS-21">21</A> Davis FA. Horner CJ. J. Org. Chem. 1973, 38: 695

<A NAME="RH58110SS-22">22</A> Miura S, Shimada M, Marui S, Tamura N, Nakada Y, Tozawa R, Sakamoto J, Funabashi Y, and Hosono H. inventors; Patent PCT Int. Appl. WO 2007052843. ; Chem. Abstr. 2007, 146, 501048

<A NAME="RH58110SS-23">23</A> Marziano N. Gazz. Chim. Ital. 1964, 94: 1137 ; Chem. Abstr. 1965, 63, 9909

<A NAME="RH58110SS-24">24</A> Miyoshi T, Asami Y, Sato M, Ishiguro M, and Kitahara T. inventors; Patent PCT Int. Appl. WO 9408956. ; Chem. Abstr. 1994, 121, 133683

<A NAME="RH58110SS-25">25</A> Fukumoto S, Watanabe T, and Ikeda S. inventors; Patent PCT Int. Appl. WO 2002018350. ; Chem. Abstr. 2002, 136, 232313

<A NAME="RH58110SS-26">26</A> Bonaterra M. Martin SE. Rossi RA. Tetrahedron Lett. 2006, 47: 3511

<A NAME="RH58110SS-27">27</A> Zhuikov VV. Russ. J. Gen. Chem. 1999, 69: 1796

<A NAME="RH58110SS-28">28</A> Matsugi M. Murata K. Gotanda K. Nambu H. Anilkumar G. Matsumoto K. Kita Y. J. Org. Chem. 2001, 66: 2434

Supplementary Material

Supporting Information

FeF3/I2-Catalyzed Synthesis of 4-Chalcogen-Substituted Arylamines by Direct Thiolation of an Arene C-H Bond

FeF₃/I₂-Catalyzed Synthesis of 4-Chalcogen-Substituted Arylamines by Direct Thiolation of an Arene C-H Bond