Advances in the Direct Amination
of Azole C-H Bonds

Ming Zhang

doi:10.1055/s-0030-1260231

REVIEW

Advances in the Direct Amination of Azole C-H Bonds

Ming Zhang*
College of Chemistry, Jiangxi Normal University , (Yaohu Campus), 99 Ziyangdadao, Nanchang, Jiangxi 330022, P. R. of China
Fax: +86(189)79135351; e-Mail: zmchem@163.com;

Abstract

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Abstract

The direct amination of azole C-H bonds provides a straightforward, effective access to nitrogen group containing azoles without the prefunctionalization of azoles. This review discussed the rapid advances in the direct amination of azoles; copper-catalyzed/mediated amination, acid-promoted amination, and metal-free amination are discussed.

1 Introduction

2 Copper-Catalyzed/Mediated Amination

3 Acid-Promoted Amination

4 Metal-Free Amination

5 Conclusions

Key words

amides - amines - amination - coupling - heterocycles

Full Text

References

<A NAME="RM70411SS-1A">1a</A> Yeung CS. Dong VM. Chem. Rev. 2011, 111: 1215

<A NAME="RM70411SS-1B">1b</A> Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011, 111: 1293

<A NAME="RM70411SS-1C">1c</A> Ackermann L. Chem. Rev. 2011, 111: 1315

<A NAME="RM70411SS-1D">1d</A> Godula K. Sames D. Science 2006, 312: 67

<A NAME="RM70411SS-1E">1e</A> Zhang M. Adv. Synth. Catal. 2009, 351: 2243

<A NAME="RM70411SS-1F">1f</A> Zhang M. Appl. Organomet. Chem. 2010, 24: 269

<A NAME="RM70411SS-1G">1g</A> Collet F. Lescot C. Dauban P. Chem. Soc. Rev. 2011, 40: 1926

<A NAME="RM70411SS-1H">1h</A> Collet F. Dodd RH. Dauban P. Chem. Commun. 2009, 5061

<A NAME="RM70411SS-1I">1i</A> Thansandote P. Lautens M. Chem. Eur. J. 2009, 15: 5874

<A NAME="RM70411SS-1J">1j</A> Muller P. Fruit C. Chem. Rev. 2003, 103: 2905

<A NAME="RM70411SS-1K">1k</A> Davies HML. Long MS. Angew. Chem. Int. Ed. 2005, 44: 3518

<A NAME="RM70411SS-1L">1l</A> Cho SH. Kim JY. Kwak J. Chang S. Chem. Soc. Rev. 2011, in press; DOI: 10.1039/C1CS15082K

<A NAME="RM70411SS-2A">2a</A> Hili R. Yudin AK. Nat. Chem. Biol. 2006, 2: 284

<A NAME="RM70411SS-2B">2b</A> Powers JP. Li SY. Jaen JC. Liu JQ. Walker NPC. Wang ZL. Wesche H. Bioorg. Med. Chem. Lett. 2006, 16: 284

<A NAME="RM70411SS-2C">2c</A> Armstrong A. Collins JC. Angew. Chem. Int. Ed. 2010, 49: 2282

<A NAME="RM70411SS-3">3</A> Hooper MW. Utsunomiya M. Hartwig JF. J. Org. Chem. 2003, 68: 2861

<A NAME="RM70411SS-4">4</A> Monguchi D. Fujiwara T. Furukawa H. Mori A. Org. Lett. 2009, 11: 1607

<A NAME="RM70411SS-5">5</A> Hamada T. Ye X. Stahl SS. J. Am. Chem. Soc. 2008, 130: 833

<A NAME="RM70411SS-6">6</A> Wang Q. Schreiber SL. Org. Lett. 2009, 11: 5178

<A NAME="RM70411SS-7">7</A> Zhao H. Wang M. Su W. Hong M. Adv. Synth. Catal. 2010, 352: 1301

<A NAME="RM70411SS-8">8</A> Huffman LM. Stahl SS. J. Am. Chem. Soc. 2008, 130: 9196

<A NAME="RM70411SS-9">9</A> Miyasaka M. Hirano K. Satoh T. Kowalczyk R. Bolm C. Miura M. Org. Lett. 2011, 13: 359

<A NAME="RM70411SS-10A">10a</A> Do H.-Q. Daugulis O. J. Am. Chem. Soc. 2007, 129: 12404

<A NAME="RM70411SS-10B">10b</A> Yoshizumi T. Tsurugi H. Satoh T. Miura M. Tetrahedron Lett. 2008, 49: 1598

<A NAME="RM70411SS-10C">10c</A> Zhao D. Wang W. Yang F. Lan J. Yang L. Gao G. You J. Angew. Chem. Int. Ed. 2009, 48: 3296 ; corrigendum: Angew. Chem. Int. Ed. 2009, 48, 4884

<A NAME="RM70411SS-10D">10d</A> Besselievre F. Piguel S. Angew. Chem. Int. Ed. 2009, 48: 9553

<A NAME="RM70411SS-10E">10e</A> Ackermann L. Potukuchi HK. Org. Biomol. Chem. 2010, 8: 4503

<A NAME="RM70411SS-10F">10f</A> Ackermann L. Potukuchi HK. Landsberg D. Vicente R. Org. Lett. 2008, 10: 3081

<A NAME="RM70411SS-10G">10g</A> Yotphan S. Bergman R. Ellman J. Org. Lett. 2009, 11: 1511

<A NAME="RM70411SS-11A">11a</A> Kitahara M. Hirano K. Tsurugi H. Satoh T. Miura M. Chem. Eur. J. 2010, 16: 1772

<A NAME="RM70411SS-11B">11b</A> Wei Y. Zhao H. Kan T. Su W. Hong M. J. Am. Chem. Soc. 2010, 132: 2522

<A NAME="RM70411SS-12A">12a</A> He C. Chen C. Cheng J. Liu C. Liu W. Li Q. Lei A. Angew. Chem. Int. Ed. 2008, 47: 6414

<A NAME="RM70411SS-12B">12b</A> Barker TJ. Jarvo ER. J. Am. Chem. Soc. 2009, 131: 15598

<A NAME="RM70411SS-12C">12c</A> Hatakeyama T. Yoshimoto Y. Chorai SK. Nakamura M. Org. Lett. 2010, 12: 1516

<A NAME="RM70411SS-12D">12d</A> Berman AM. Johnson JS. J. Am. Chem. Soc. 2004, 126: 5680

<A NAME="RM70411SS-12E">12e</A> Tan Y. Hartwig JF. J. Am. Chem. Soc. 2010, 132: 3676

<A NAME="RM70411SS-13A">13a</A> Kawano T. Hirano K. Satoh T. Miura M. J. Am. Chem. Soc. 2010, 132: 6900

<A NAME="RM70411SS-13B">13b</A> Matsuda N. Hirano K. Satoh T. Miuru M. Org. Lett. 2011, 13: 2860

<A NAME="RM70411SS-14A">14a</A> Srieter ER. Bhayann B. Buchwald SL. J. Am. Chem. Soc. 2009, 131: 78

<A NAME="RM70411SS-14B">14b</A> King AE. Brunold TC. Stahl SS. J. Am. Chem. Soc. 2009, 131: 5044

<A NAME="RM70411SS-15">15</A> Guo S. Qian B. Xie Y. Xia C. Huang H. Org. Lett. 2011, 13: 522

<A NAME="RM70411SS-16A">16a</A> Kuninobu Y. Nishi M. Takai K. Chem. Commun. 2010, 46: 8860

<A NAME="RM70411SS-16B">16b</A> Kruger K. Tillack A. Beller M. ChemSusChem 2009, 2: 715

<A NAME="RM70411SS-16C">16c</A> Ueno S. Chatani N. Kakiuchi F. J. Am. Chem. Soc. 2007, 129: 6098

<A NAME="RM70411SS-16D">16d</A> Zou B. Jiang H.-F. Wang Z.-Y. Eur. J. Org. Chem. 2007, 4600

<A NAME="RM70411SS-16E">16e</A> Laine RM. Thomas DW. Cary LW. J. Am. Chem. Soc. 1982, 104: 1763

<A NAME="RM70411SS-17A">17a</A> Lewis EA. Tolman WB. Chem. Rev. 2004, 104: 1047

<A NAME="RM70411SS-17B">17b</A> Mirica LM. Ottenwaelder X. Stack TDP. Chem. Rev. 2004, 104: 1013

<A NAME="RM70411SS-17C">17c</A> Prigge ST. Eipper BA. Mains RE. Amzel LM. Science 2004, 304: 864

<A NAME="RM70411SS-17D">17d</A> Nam W. Acc. Chem. Res. 2007, 40: 465

<A NAME="RM70411SS-17E">17e</A> Tian J.-S. Loh T.-P. Angew. Chem. Int. Ed. 2010, 49: 8417

<A NAME="RM70411SS-17F">17f</A> Giri R. Hartwig JF. J. Am. Chem. Soc. 2010, 132: 15860

<A NAME="RM70411SS-18">18</A> Cho SH. Kim JY. Lee SY. Chang S. Angew. Chem. Int. Ed. 2009, 48: 9127

<A NAME="RM70411SS-19A">19a</A> Coalter JN. Huffman JC. Caulton KG. Organometallics 2000, 19: 3569

<A NAME="RM70411SS-19B">19b</A> Serp P. Hernandez M. Richard B. Kalck P. Eur. J. Inorg. Chem. 2001, 2327

<A NAME="RM70411SS-20A">20a</A> Weibel JM. Blanc A. Plale P. Chem. Rev. 2008, 108: 3149

<A NAME="RM70411SS-20B">20b</A> Alvarez-Corral M. Munoz-Dorado M. Rodriguez-Garcoa I. Chem. Rev. 2008, 108: 3174

<A NAME="RM70411SS-20C">20c</A> Furuy T. Strom AE. Ritter T. J. Am. Chem. Soc. 2009, 131: 1662

<A NAME="RM70411SS-20D">20d</A> Chen Y.-X. Qian L.-F. Zhang W. Han B. Angew. Chem. Int. Ed. 2008, 47: 9330

<A NAME="RM70411SS-20E">20e</A> Jia Y.-X. Kundig EP. Angew. Chem. Int. Ed. 2009, 48: 1636

<A NAME="RM70411SS-21A">21a</A> Scott EJY. J. Phys. Chem. 1970, 74: 1174

<A NAME="RM70411SS-21B">21b</A> Houghton RP. Rice CR. Polyhedron 1996, 15: 1895

<A NAME="RM70411SS-21C">21c</A> Johnson NA. Gould ES. J. Am. Chem. Soc. 1973, 95: 5198

<A NAME="RM70411SS-21D">21d</A> Sawyer DT. Sobkowiak A. Matsushita T. Acc. Chem. Res. 1996, 29: 409

<A NAME="RM70411SS-22">22</A> Kim JY. Cho SH. Joseph J. Chang S. Angew. Chem. Int. Ed. 2010, 49: 9899

<A NAME="RM70411SS-23">23</A> Li Y. Xie Y. Zhang R. Jin K. Wang X. Duan C. J. Org. Chem. 2011, 76: 5444

<A NAME="RM70411SS-24A">24a</A> Bolm C. Legros J. Paih JL. Zani L. Chem. Rev. 2004, 104: 6217

<A NAME="RM70411SS-24B">24b</A> Enthaler S. Junge K. Beller M. Angew. Chem. Int. Ed. 2008, 47: 3317

<A NAME="RM70411SS-24C">24c</A> Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011, 111: 1293

<A NAME="RM70411SS-24D">24d</A> Zhang M. Zhang A. Appl. Organomet. Chem. 2010, 24: 751

<A NAME="RM70411SS-25">25</A> Wang J. Hou J.-T. Wen J. Zhang J. Yu X.-Q. Chem. Commun. 2011, 47: 3652

<A NAME="RM70411SS-26">26</A> Joseph J. Kim JY. Chang S. Chem. Eur. J. 2011, 17: 8294

<A NAME="RM70411SS-27">27</A> Varma RS. Saini RK. Prakash O. Tetrahedron Lett. 1997, 38: 2621

<A NAME="RM70411SS-28">28</A> Froehr T. Sindlinger CP. Kloeckner U. Finkbeiner P. Nachtscheim BJ. Org. Lett. 2011, 13: 3754

<A NAME="RM70411SS-29A">29a</A> Uyanik M. Suzuki D. Yasui T. Ishihara K. Angew. Chem. Int. Ed. 2011, 50: 5331

<A NAME="RM70411SS-29B">29b</A> Chen L. Shi E. Liu Z. Chen S. Wei W. Li H. Xu K. Wan X. Chem. Eur. J. 2011, 17: 4085

<A NAME="RM70411SS-29C">29c</A> Rodriguez A. Moran WJ. Org. Lett. 2011, 13: 2220

<A NAME="RM70411SS-30">30</A> Urbansky ET. Cooper BT. Margerum DW. Inorg. Chem. 1997, 36: 1338