Efficient Preparation of ortho-Aminobenzenesulfonamides using
Ligand-Free Copper(I)-Catalyzed Amination

Zineb Bahlaouan; Jérôme Thibonnet; Alain Duchêne; Jean-Luc Parrain; Mostafa Elhilali; Mohamed Abarbri

doi:10.1055/s-0030-1260323

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2011(17): 2509-2512
DOI: 10.1055/s-0030-1260323

LETTER

Efficient Preparation of ortho-Aminobenzenesulfonamides using Ligand-Free Copper(I)-Catalyzed Amination

Zineb Bahlaouan^a, Jérôme Thibonnet^a, Alain Duchêne^a, Jean-Luc Parrain^b, Mostafa Elhilali^a, Mohamed Abarbri*^a
^a Laboratoire de Physicochimie des Matériaux et Biomolécules, EA 4244, Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: mohamed.abarbri@univ-tours.fr;
^b Institut des Sciences Moléculaires de Marseille, iSm2 UMR CNRS 6263, Campus Scientifique de Saint Jérôme, Aix-Marseille Université, 13397 Marseille, France

Further Information

Publication History

Received 10 June 2011
Publication Date:
22 September 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A general and efficient method of copper-catalyzed amination of 2-iodobenzenesulfonamide has been developed under very mild conditions, with good to excellent yields. This method uses inexpensive copper(I) iodide as catalyst, readily available 2-iodobenzenesulfonamides and aliphatic amines as the starting materials, and does not require the use of any ligand system or any expensive supplementary additives.

Key words

2-iodobenzenesulfonamide - copper(I) catalyst - N-arylation - ligand-free - 2-aminobenzenesulfonamides

References and Notes

1 Hester B. Gibson JK. Cimini MG. Emmert DE. Locker PK. Perricone SC. Skaletzky LL. Sykes JK. West BE. J. Med. Chem. 1991, 34: 308

Crossref Google Scholar
2 Romero DL. Morge RA. Genin MJ. Biles C. Busso M. Resnick L. Althaus IW. Reusser F. Thomas RC. Tarpley WG. J. Med. Chem. 1993, 36: 1505

Crossref Google Scholar
3 Serradeil-Le Gal C. Wagnon J. Garcia C. Lacour C. Guiraudou P. Christophe B. Villanova G. Nisato D. Maffrand JP. J. Clin. Invest. 1993, 92: 224

Crossref Google Scholar
4 Turner SR. Strohbach JW. Tommasi RA. Aristoff PA. Johnson PD. Skulnick HI. Dolak LA. Seest EP. Tomich PK. Bohanon MJ. Horng MM. Lynn JC. Chong K.-T. Hinshaw RR. Watenpaugh KD. Janakiraman MN. Thaisrivongs S. J. Med. Chem. 1998, 41: 3467

Crossref Google Scholar
5a Northey EH. The Sulfonamides and Allied Compounds Reinhold; New York: 1948. p.3-339

Google Scholar
5b Clare BW. Supuran CT. Eur. J. Med. Chem. 1999, 34: 463

Google Scholar
6a Ullmann F. Ber. Dtsch. Chem. Ges. 1903, 36: 2382

Google Scholar
6b Goldberg I. Ber. Dtsch. Chem. Ges. 1906, 39: 1691

Google Scholar
6c Lindley J. Tetrahedron 1984, 40: 1433

Google Scholar
6d Goodbrand HB. Hu N.-X. J. Org. Chem. 1999, 64: 670

Google Scholar
6e Arterbum JB. Pennala M. Gonzalez AM. Tetrahedron Lett. 2001, 42: 1475

Google Scholar
6f Lang F. Zewge D. Houpis IN. Volante RP. Tetrahedron Lett. 2001, 42: 3251

Google Scholar
7a Kaddouri H. Vicente V. Ouali A. Ouazzani F. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 333

Google Scholar
7b Xia N. Taillefer M. Angew. Chem. Int. Ed. 2009, 48: 337

Google Scholar
7c Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

Google Scholar
7d Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

Google Scholar
7e Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

Google Scholar
7f Gujadhur RK. Bates CG. Venkataraman D. Org. Lett. 2001, 3: 4315

Google Scholar
7g van Allen D. Venkataraman D. J. Org. Chem. 2003, 68: 4590

Google Scholar
7h Cristau H.-J. Cellier PP. Spindler J.-F. Taillefer M. Eur. J. Org. Chem. 2004, 695

Google Scholar
7i Cristau H.-J. Cellier PP. Spindler J.-F. Taillefer M. Chem. Eur. J. 2004, 10: 5607

Google Scholar
7j Zhang S. Zhang D. Liebeskind LS. J. Org. Chem. 1997, 62: 2312

Google Scholar
7k Kelkar AA. Patil NM. Chaudhari RV. Tetrahedron Lett. 2002, 43: 7143

Google Scholar
7l Gajare AS. Toyota K. Yoshifuji M. Yoshifuji F. Chem. Commun. 2004, 1994

Google Scholar
7m Rao H. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2005, 70: 8107

Google Scholar
7n Guo X. Rao H. Fu H. Jiang Y. Zhao Y. Adv. Synth. Catal. 2006, 384: 2197

Google Scholar
8a Okano K. Tokuyama H. Fukuyama T. Org. Lett. 2003, 5: 4987

Google Scholar
8b Kwong FY. Buchwald SL. Org. Lett. 2003, 5: 793

Google Scholar
9a Ma D. Zhang Y. Yao J. Wu S. Tao F. J. Am. Chem. Soc. 1998, 120: 12459

Google Scholar
9b Ma D. Cai Q. Zhang H. Org. Lett. 2003, 5: 2453

Google Scholar
9c Zhang H. Cai Q. Ma D. J. Org. Chem. 2005, 70: 5164

Google Scholar
10a Lu Z. Twieg RJ. Huang SD. Tetrahedron Lett. 2003, 44: 6289

Google Scholar
10b Lu Z. Twieg RJ. Tetrahedron 2005, 61: 903

Google Scholar
11 Zhang Z. Mao J. Zhu D. Wu F. Chen H. Wan B. Tetrahedron 2006, 62: 4435

Crossref Google Scholar
12 Xu L. Zhu D. Wu F. Wang R. Wan B. Tetrahedron 2005, 61: 6553

Crossref Google Scholar
13 Shafir A. Buchwald SL. J. Am. Chem. Soc. 2006, 128: 8742

Crossref PubMed Google Scholar
14 Zeng L. Fu H. Qiao R. Jiang Y. Zhao Y. Adv. Synth. Catal. 2009, 351: 1671

Crossref Google Scholar
15a He H. Wu Y.-J. Tetrahedron Lett. 2003, 44: 3385

Google Scholar
15b Correa A. Bolm C. Adv. Synth. Catal. 2007, 349: 2673

Google Scholar
15c Zhu R. Xing L. Wang X. Cheng C. Su D. Hu Y. Adv. Synth. Catal. 2008, 350: 1253

Google Scholar
15d Huang YZ. Miao H. Zhang Q.-H. Chen C. Xu J. Catal. Lett. 2008, 122: 344

Google Scholar
15e Bellina F. Calandri C. Cauteruccio S. Rossi R. Eur. J. Org. Chem. 2007, 2147

Google Scholar
15f Chang JWW. Xu X. Chan PWH. Tetrahedron Lett. 2007, 48: 245

Google Scholar
15g Sperotto E. de Vries JG. van Klink GPM. van Koten G. Tetrahedron Lett. 2007, 48: 7366

Google Scholar
15h Rout L. Jammi S. Punniyamurthy T. Org. Lett. 2007, 9: 3397

Google Scholar
15i Xu H. Wolf C. Chem. Commun. 2009, 1715

Google Scholar
15j Yong FF. Teo YC. Synlett 2010, 3068

Google Scholar
15k Teo YC. Yong FF. Synlett 2011, 837

Google Scholar
15l Azzaro S. Desage-El Murr M. Fensterbank L. Lacôte E. Malacria M. Synlett 2011, 849

Google Scholar
16a Rolfe A. Hanson PR. Tetrahedron Lett. 2009, 50: 6935

Google Scholar
16b Rolfe A. Lushington GH. Hanson PR. Org. Biomol. Chem. 2010, 8: 2198

Google Scholar
17 Inack-Ngi S. Rahmani R. Commeiras L. Chouraqui G. Thibonnet J. Duchêne A. Abarbri M. Parrain J.-L. Adv. Synth. Catal. 2009, 351: 779

Crossref Google Scholar
18 Chau MM. Kice JL. J. Org. Chem. 1977, 42: 3265

Crossref Google Scholar
19 Blanchet J. Macklin T. Ang P. Metallinos C. Snieckus V. J. Org. Chem. 2007, 72: 3199

Crossref Google Scholar

20

Typical Experimental Procedure for the Synthesis of N -Benzyl-2-(propargylamino)benzenesulfonamide (2c): 2-Iodobenzenesulfonamide (300 mg, 1 mmol), K₂CO₃ (138 mg, 1 mmol) and anhyd DMF (10 mL) were introduced into a dry Schlenk flask under argon. The mixture was cooled to 0 ˚C and degassed under agitation (10 min). Then amine (1.1 mmol) and CuI (19 mg, 0.1 mmol) were introduced successively under argon flux. The mixture was brought to r.t. and left under stirring for 12 h. The reaction mixture was diluted with Et₂O, washed with aq NH₄Cl and H₂O, dried over MgSO₄, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel (petroleum ether-Et₂O, 50:50) or by crystallization (petroleum ether-CH₂Cl₂, 80:20); yield: 79%; white solid; mp 64-66 ˚C. IR (KBr): 1599, 2114, 2963, 3252, 3389 cm^-¹. ^¹H NMR (200 MHz, CDCl₃): δ = 7.79 (dd, J = 7.9, 1.3 Hz, 1 H), 7.47 (td, J = 7.9, 1.3 Hz, 1 H), 7.13-7.26 (m, 5 H), 6.79-6.91 (m, 2 H), 6.06 (t, J = 5.4 Hz, 1 H), 5.25 (t, J = 6.2 Hz, 1 H), 3.94-4.06 (m, 4 H), 2.24 (t, J = 2.4 Hz, 1 H). ^¹³C NMR (50 MHz, CDCl₃): δ = 144.2, 139.4, 135.7, 134.0, 129.8, 128.2 (2 × C), 127.4 (2 × C), 121.4, 116.9, 112.6, 79.5, 71.4, 46.8, 32.4. MS (EI): m/z = 300 [M] (8), 130 (51), 129 (59), 108, 106 (100), 102 (22), 91 (63). Anal. Calcd for C₁₆H₁₆N₂O₂S: C, 63.98; H, 5.37; N, 9.33. Found: C, 63.83; H, 5.41; N, 9.35.