N-Arylations of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides Using a Copper(I) Oxide Nanoparticle/1,10-Phenanthroline Catalytic System

Bo-Xiao Tang; Sheng-Mei Guo; Man-Bo Zhang; Jin-Heng Li

doi:10.1055/s-2008-1067014

PAPER

N-Arylations of Nitrogen-Containing Heterocycles with Aryl and Heteroaryl Halides Using a Copper(I) Oxide Nanoparticle/1,10-Phenanthroline Catalytic System

Bo-Xiao Tang, Sheng-Mei Guo, Man-Bo Zhang, Jin-Heng Li*
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)8872531; e-Mail: jhli@hunnu.edu.cn;

Abstract

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Abstract

A general procedure for solvent-free N-arylations of nitrogen-containing heterocycles, i.e. imidazoles, triazoles, and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu₂O) nanoparticles is demonstrated. Four types of Cu₂O were evaluated: the bulky compound and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu₂O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu₂O nanoparticles, 1,10-phenanthroline, and tetrabutylammonium fluoride, a variety of nitrogen-containing heterocycles smoothly underwent N-arylation with aryl and heteroaryl halides at 110-145 °C to give the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under solvent-free conditions. The reaction mechanism is also discussed.

Key words

copper(I) oxide nanoparticles - 1,10-phenanthroline - N-arylations - heterocycles - halides

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Referenzen

References

For selected recent examples, see:

<A NAME="RF01708SS-1A">1a</A> Zhong C. He J. Xue C. Li Y. Bioorg. Med. Chem. 2004, 12: 4009

<A NAME="RF01708SS-1B">1b</A> Dyck B. Goodfellow VS. Phillips T. Grey J. Haddach M. Rowbottom M. Naeve GS. Brown B. Saunders J. Bioorg. Med. Chem. Lett. 2004, 14: 1151

<A NAME="RF01708SS-1C">1c</A> Smallheer JM. Alexander RS. Wang J. Wang S. Nakajima S. Rossi KA. Smallwood A. Barbera F. Burdick D. Luettgen JM. Knabb RM. Wexler RR. Jadhav PK. Bioorg. Med. Chem. Lett. 2004, 14: 5263

<A NAME="RF01708SS-1D">1d</A> Qiao JX. Cheng X. Modi DP. Rossi KA. Luettgen JM. Knabb RM. Jadhav PK. Wexler RR. Bioorg. Med. Chem. Lett. 2005, 15: 29

<A NAME="RF01708SS-1E">1e</A> Mano T. Okumura Y. Sakakibara M. Okumura T. Tamura T. Miyamoto K. Stevens RW. J. Med. Chem. 2004, 47: 720

<A NAME="RF01708SS-1F">1f</A> Roppe J. Smith ND. Huang D. Tehrani L. Wang B. Anderson J. Brodkin J. Chung J. Jiang X. King C. Munoz B. Varney MA. Prasit P. Cosford NDP. J. Med. Chem. 2004, 47: 4645

<A NAME="RF01708SS-1G">1g</A> Venkatesan AM. Gu Y. Santos OD. Abe T. Agarwal A. Yang Y. Petersen PJ. Weiss WJ. Mansour TS. Nukaga M. Hujer AM. Bonomo RA. Knox JR. J. Med. Chem. 2004, 47: 6556

<A NAME="RF01708SS-1H">1h</A> Lange JHM. van Stuivenberg HH. Coolen HKAC. Adolfs TJP. McCreary AC. Keizer HG. Wals HC. Veerman W. Borst AJM. de Looff W. Verveer PC. Kruse CG. J. Med. Chem. 2005, 48: 1823

<A NAME="RF01708SS-1I">1i</A> Quan ML. Lam PYS. Han Q. Pinto DJP. He MY. Li R. Ellis CD. Clark CG. Teleha CA. Sun J.-H. Alexander RS. Bai S. Luettgen JM. Knabb RM. Wong PC. Wexler RR. J. Med. Chem. 2005, 48: 1729

<A NAME="RF01708SS-1J">1j</A> Barchéchath SD. Tawatao RI. Corr M. Carson DA. Cottam HB. J. Med. Chem. 2005, 48: 6409

<A NAME="RF01708SS-1K">1k</A> Voets M. Antes I. Scherer C. Müller-Vieira U. Biemel K. Barassin C. Marchais-Oberwinkler S. Hartmann RW. J. Med. Chem. 2005, 48: 6632

<A NAME="RF01708SS-1L">1l</A> Wiglenda T. Ott I. Kircher B. Schumacher P. Schuster D. Langer T. Gust R. J. Med. Chem. 2005, 48: 6516

<A NAME="RF01708SS-1M">1m</A> Jiang W. Guan J. Macielag MJ. Zhang S. Qiu Y. Kraft P. Bhattacharjee S. John TM. Haynes-Johnson D. Lundeen S. Sui Z. J. Med. Chem. 2005, 48: 2126

<A NAME="RF01708SS-1N">1n</A> Mahboobi S. Sellmer A. Hocher H. Eichhorn E. Bar T. Schmidt M. Maier T. Stadlwieser JF. Beckers TL. J. Med. Chem. 2006, 49: 5769

For selected papers on palladium-catalyzed N-arylations of imidazoles, see:

<A NAME="RF01708SS-2A">2a</A> Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis Negishi E. Wiley Interscience; New York: 2002. p.1051

<A NAME="RF01708SS-2B">2b</A> Jiang L. Buchwald SL. In Metal-Catalyzed Cross-Coupling Reactions de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. p.699

<A NAME="RF01708SS-2C">2c</A> Bellina F. Cauteruccio S. Mannina L. Rossi R. Viel S. J. Org. Chem. 2005, 70: 3997

For selected reviews on the use of copper as the catalyst, see:

<A NAME="RF01708SS-3A">3a</A> Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337

<A NAME="RF01708SS-3B">3b</A> Ley SV. Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400

<A NAME="RF01708SS-4">4</A> For a paper on N-arylations of imidazoles with aryl halides mediated by stoichiometric copper, see: Lindley J. Tetrahedron 1984, 40: 1433

<A NAME="RF01708SS-5A">5a</A> Kiyomori A. Marcoux JF. Buchwald SL. Tetrahedron Lett. 1999, 40: 2657

<A NAME="RF01708SS-5B">5b</A> Kuil M. Bekedam EK. Visser GM. van den Hoogenband A. Terpstra JW. Kamer PCJ. Kamer van Leeuwen PWNM. van Strijdonck GPF. Tetrahedron Lett. 2005, 46: 2405

<A NAME="RF01708SS-5C">5c</A> Altman RA. Buchwald SL. Org. Lett. 2006, 8: 2779

<A NAME="RF01708SS-5D">5d</A> Altman RA. Koval ED. Buchwald SL. J. Org. Chem. 2007, 72: 6190

<A NAME="RF01708SS-5E">5e</A> Hosseinzadeh R. Tajbakhsh M. Alikarami M. Synlett 2006, 2124

<A NAME="RF01708SS-6A">6a</A> Klapars A. Antilla JC. Huang X. Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727

<A NAME="RF01708SS-6B">6b</A> Alcalde E. Dinarès I. Rodríguez S. Garcia de Miguel C. Eur. J. Org. Chem. 2005, 1637

<A NAME="RF01708SS-6C">6c</A> Antilla JC. Baskin JM. Barder TE. Buchwald SL. J. Org. Chem. 2004, 69: 5578

<A NAME="RF01708SS-7">7</A> Jerphagnon T. van Klink GPM. de Vries JG. van Koten G. Org. Lett. 2005, 7: 5241

<A NAME="RF01708SS-8A">8a</A> Ma D. Cai Q. Synlett 2004, 128

<A NAME="RF01708SS-8B">8b</A> Zhang H. Cai Q. Ma D. J. Org. Chem. 2005, 70: 5164

<A NAME="RF01708SS-8C">8c</A> Lv X. Wang Z. Bao W. Tetrahedron 2006, 62: 4756

<A NAME="RF01708SS-8D">8d</A> Deng W. Wang YF. Zhang C. Liu L. Guo QX. Chin. Chem. Lett. 2006, 17: 313

<A NAME="RF01708SS-9">9</A> Liu L. Frohn M. Xi N. Dominguez C. Hungate R. Reider PJ. J. Org. Chem. 2005, 70: 10135

<A NAME="RF01708SS-10">10</A> Rao H. Fu H. Jiang Y. Zhao Y. J. Org. Chem. 2005, 70: 8107

<A NAME="RF01708SS-11">11</A> Xu L. Zhu D. Wu F. Wang R. Wan B. Tetrahedron 2005, 61: 6553

<A NAME="RF01708SS-12A">12a</A> Zhang Z. Mao J. Zhu D. Wu F. Chen H. Wan B. Tetrahedron 2006, 62: 4435

<A NAME="RF01708SS-12B">12b</A> Yang M. Liu F. J. Org. Chem. 2007, 72: 8969

<A NAME="RF01708SS-13">13</A> Xie Y.-X. Pi S.-F. Wang J. Yin D.-L. Li J.-H. J. Org. Chem. 2006, 71: 8324

<A NAME="RF01708SS-14">14</A> Zhu L. Cheng L. Zhang Y. Xie R. You J. J. Org. Chem. 2007, 72: 2737

<A NAME="RF01708SS-15">15</A> Huang Y.-Z. Gao J. Ma H. Miao H. Xu J. Tetrahedron Lett. 2008, 49: 948

<A NAME="RF01708SS-16A">16a</A> Choudary BM. Sridhar C. Kantam ML. Venkanna GT. Sreedhar B. J. Am. Chem. Soc. 2005, 127: 9948

<A NAME="RF01708SS-16B">16b</A> Son SU. Park IK. Park J. Hyeon T. Chem. Commun. 2004, 778

<A NAME="RF01708SS-16C">16c</A> Taillefer M. Xia N. Ouali A. Angew. Chem. Int. Ed. 2007, 46: 934

<A NAME="RF01708SS-16D">16d</A> Kantam ML. Rao BPC. Choudary BM. Reddy RS. Synlett 2006, 2195

<A NAME="RF01708SS-16E">16e</A> Zhu L. Guo P. Li G. Lan J. Xie R. You J. J. Org. Chem. 2007, 72: 8535

For selected representative papers on copper-catalyzed N-arylations of imidazoles with other reagents, see:

<A NAME="RF01708SS-17A">17a</A> Lopez-Alvarado P. Avendaño C. Menéndez JC. J. Org. Chem. 1995, 60: 5678

<A NAME="RF01708SS-17B">17b</A> Collman JP. Zhong M. Org. Lett. 2000, 2: 1233

<A NAME="RF01708SS-17C">17c</A> Collman JP. Zhong M. Zeng L. Costanzo S. J. Org. Chem. 2001, 66: 1528

<A NAME="RF01708SS-17D">17d</A> Collman JP. Zhong M. Zhang C. Costanzo S. J. Org. Chem. 2001, 66: 7892

<A NAME="RF01708SS-17E">17e</A> Lan J.-B. Chen L. Yu X.-Q. You J.-S. Xie R.-G. Chem. Commun. 2004, 188

<A NAME="RF01708SS-17F">17f</A> Lam PYS. Deudon S. Averill KM. Li R. He MY. DeShong P. Clark CG. J. Am. Chem. Soc. 2000, 122: 7600

<A NAME="RF01708SS-17G">17g</A> Fedorov AY. Finet J.-P. Tetrahedron Lett. 1999, 40: 2747

<A NAME="RF01708SS-17H">17h</A> Kang S.-K. Lee S.-H. Lee D. Synlett 2000, 1022

<A NAME="RF01708SS-17I">17i</A> Lam PYS. Clark CG. Saubern S. Adams J. Averill KM. Chan DMT. Combs A. Synlett 2000, 674

<A NAME="RF01708SS-17J">17j</A> Kantam ML. Venkanna GT. Sridhar C. Sreedhar B. Choudary BM. J. Org. Chem. 2006, 71: 9522

For selected papers on N-arylations of indoles using palladium, see:

<A NAME="RF01708SS-18A">18a</A> Old DW. Harris MC. Buchwald SL. Org. Lett. 2000, 2: 1403

<A NAME="RF01708SS-18B">18b</A> Movassaghi M. Ondrus AE. J. Org. Chem. 2005, 70: 8638

Using copper, see:

<A NAME="RF01708SS-18C">18c</A> Antilla JC. Klapars A. Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684

<A NAME="RF01708SS-18D">18d</A> Chandrasekhar S. Sultana SS. Yaragorla SR. Reddy NR. Synthesis 2006, 839

<A NAME="RF01708SS-18E">18e</A> Zhou T. Chen Z.-C. Synth. Commun. 2002, 32: 903

<A NAME="RF01708SS-18F">18f</A> Bekolo H. Can. J. Chem. 2007, 85: 42

<A NAME="RF01708SS-19">19</A> Rout L. Jammi T. Punniyamurthy B.-X. Org. Lett. 2007, 9: 3397

<A NAME="RF01708SS-20">20</A> Tang B.-X. Wang F. Li J.-H. Xie Y.-X. Zhang MB. J. Org. Chem. 2007, 72: 6294

<A NAME="RF01708SS-21">21</A> For a paper on solvent-free, copper-catalyzed amination reactions of aryl halides with amines, see: Gajare AS. Toyota K. Yoshifuji M. Ozawa F. Chem. Commun. 2004, 1994

<A NAME="RF01708SS-22">22</A> Zhang S.-L. Liu L. Fu Y. Guo Q.-X. Organometallics 2007, 26: 4546

For representative papers on transition-metal-catalyzed cross-coupling reactions promoted by quaternary ammonium compounds, in particular TBAB, see:

<A NAME="RF01708SS-23A">23a</A> Badone D. Baroni M. Cardamone R. Ielmini A. Guzzi U. J. Org. Chem. 1997, 62: 7170

<A NAME="RF01708SS-23B">23b</A> Bedford RB. Blake ME. Butts CP. Holder D. Chem. Commun. 2003, 466

<A NAME="RF01708SS-23C">23c</A> Lysén M. Köhler K. Synlett 2005, 1671

<A NAME="RF01708SS-23D">23d</A> Arvela RK. Leadbeater NE. Org. Lett. 2005, 7: 2101

<A NAME="RF01708SS-23E">23e</A> Liu W.-J. Xie Y.-X. Liang Y. Li J.-H. Synthesis 2006, 860

<A NAME="RF01708SS-24">24</A> Sundberg RJ. Mente DC. Yilmaz I. Gupta G. J. Heterocycl. Chem. 1977, 14: 1279

<A NAME="RF01708SS-25">25</A> Asproni B. Talani G. Busonero F. Pau A. Sanna S. Cerri R. Mascia MP. Sanna E. Biggio G. J. Med. Chem. 2005, 48: 2638

<A NAME="RF01708SS-26">26</A> Lampe JW. Di Meo SV. Traina JA. J. Heterocycl. Chem. 1994, 31: 287

<A NAME="RF01708SS-27">27</A> Lam PY. Clark CG. Sauber S. Adams J. Winters MP. Chan DM. Combs A. Tetrahedron Lett. 1998, 39: 2941

<A NAME="RF01708SS-28">28</A> Le Z.-G. Chen Z.-C. Hu Y. Zheng Q.-G. J. Chem. Res. 2004, 344

<A NAME="RF01708SS-29">29</A> Nonoyama M. Nakajima K. Polyhedron 1998, 18: 533