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Synthesis 2011(14): 2223-2236  
DOI: 10.1055/s-0030-1260082
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Photoinduced Cleavage of N-N Bonds of Aromatic Hydrazines and Hydrazides by Visible Light

Mingzhao Zhu, Nan Zheng*
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA
Fax: +1(479)5754049; e-Mail: nzheng@uark.edu;
Further Information

Publication History

Received 16 April 2011
Publication Date:
21 June 2011 (online)

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Abstract

A photocatalytic system involving [Ru(bpyrz)3](PF6)2˙2H2O, visible light, and air has been developed for cleavage of the N-N bonds of hydrazines and hydrazides. This catalytic system is generally effective for N,N-disubstituted hydrazine and hydrazide derivatives, including arylhydrazides, N-alkyl-N-arylhydrazines, and N,N-diarylhydrazines. The utility of this cleavage reaction has been demonstrated by synthesizing a variety of secondary aromatic amines.

Key words

nitrogen-nitrogen bonds - visible light - cleavage - ruthenium - amines

    References

  • For reviews, see:
  • 1a Zeitler K. Angew. Chem. Int. Ed.  2009,  48:  9785 
    Google Scholar
  • 1b Ravelli D. Dondi D. Fagnoni M. Albini A. Chem. Soc. Rev.  2009,  38:  1999 
    Google Scholar
  • 1c Narayanam JMR. Stephenson CRJ. Chem. Soc. Rev.  2011,  40:  102 
    Google Scholar
  • For photophysical and redox properties of Ru(II), see:
  • 2a Campagana S. Puntoriero F. Nastasi F. Bergamini G. Balzani V. Top. Curr. Chem.  2007,  280:  117 
    Google Scholar
  • 2b Juris A. Balzani V. Barigelletti F. Campagna S. Belser P. von Zelewsky A. Coord. Chem. Rev.  1988,  84:  85 
    Google Scholar
  • 2c Kalyanasundaram K. Grätzel M. Coord. Chem. Rev.  1998,  177:  347 
    Google Scholar
  • 2d Kalyanasundaram K. Coord. Chem. Rev.  1982,  46:  159 
    Google Scholar
  • 2e Balzani V. Bergamini G. Marchioni F. Ceroni P. Coord. Chem. Rev.  2006,  250:  1254 
    Google Scholar
  • For photophysical and redox properties of Ir(III), see:
  • 3a Lowry MS. Bernhard S. Chem. Eur. J.  2006,  12:  7970 
    Google Scholar
  • 3b Flamigni L. Barbieri A. Sabatini C. Ventura B. Barigelletti F. Top. Curr. Chem.  2007,  281:  143 
    Google Scholar
  • For early applications of Ru(II) as a photocatalyst in organic synthesis, see:
  • 4a DeLaive PJ. Giannotti C. Whitten DG. J. Am. Chem. Soc.  1978,  100:  7413 
    Google Scholar
  • 4b DeLaive PJ. Sullivan BP. Meyer TJ. Whitten DG. J. Am. Chem. Soc.  1979,  101:  4007 
    Google Scholar
  • 4c DeLaive PJ. Foreman TK. Giannotti C. Whitten DG. J. Am. Chem. Soc.  1980,  102:  5627 
    Google Scholar
  • 4d Montserrat K. Foreman TK. Gratzel M. Whitten DG. J. Am. Chem. Soc.  1981,  103:  6667 
    Google Scholar
  • 4e Pac C. Ihama M. Yasuda M. Miyauchi Y. Sakurai H. J. Am. Chem. Soc.  1981,  103:  6495 
    Google Scholar
  • 4f Cano-Yelo H. Deronzier A. J. Chem. Soc., Perkin Trans. 2  1984,  1093 
    Google Scholar
  • 4g Ishitani O. Yanagida S. Takamuku S. Pac C. J. Org. Chem.  1987,  52:  2790 
    Google Scholar
  • 4h Zen J.-M. Liou S.-L. Kumar AS. Hsia MS. Angew. Chem. Int. Ed.  2003,  42:  577 
    Google Scholar
  • 4i Okada K. Okamoto K. Morita N. Okubo K. Oda M. J. Am. Chem. Soc.  1991,  113:  9401 
    Google Scholar
  • Recent applications of Ru(II) and Ir(III) as photocatalysts in organic synthesis. Stephenson’s group:
  • 5a Narayanam JMR. Tucker JW. Stephenson CRJ. J. Am. Chem. Soc.  2009,  131:  8756 
    Google Scholar
  • 5b Tucker JW. Narayanam JMR. Krabbe SW. Stephenson CRJ. Org. Lett.  2010,  12:  368 
    Google Scholar
  • 5c Tucker JW. Nguyen JD. Narayanam JMR. Krabbe SW. Stephenson CRJ. Chem. Commun.  2010,  46:  4985 
    Google Scholar
  • 5d Furst L. Matsuura BS. Narayanam JMR. Tucker JW. Stephenson CRJ. Org. Lett.  2010,  12:  3104 
    Google Scholar
  • 5e Condie AG. González-Gómez JC. Stephenson CRJ. J. Am. Chem. Soc.  2010,  132:  1464 
    Google Scholar
  • MacMillan’s group:
  • 5f Nicewicz D. MacMillan DWC. Science  2008,  322:  77 
    Google Scholar
  • 5g Nagib DA. Scott ME. MacMillan DWC. J. Am. Chem. Soc.  2009,  131:  10875 
    Google Scholar
  • 5h Shih H.-W. Vander Wal MN. Grange RL. MacMillan DWC. J. Am. Chem. Soc.  2010,  132:  13600 
    Google Scholar
  • Yoon’s group:
  • 5i Ischay MA. Anzovino ME. Du J. Yoon TP. J. Am. Chem. Soc.  2008,  130:  12886 
    Google Scholar
  • 5j Du J. Yoon TP. J. Am. Chem. Soc.  2009,  131:  14604 
    Google Scholar
  • 5k Yoon TP. Ischay MA. Du J. Nature Chem.  2010,  2:  527 
    Google Scholar
  • 5l Ischay MA. Lu Z. Yoon TP. J. Am. Chem. Soc.  2010,  132:  8572 
    Google Scholar
  • Other groups:
  • 5m Koike T. Akita M. Chem. Lett.  2009,  38:  166 
    Google Scholar
  • 5n Hasegawa E. Takizawa S. Seida T. Yamaguchi A. Yamaguchi N. Chiba N. Takahashi T. Ikeda H. Akiyama K. Tetrahedron  2006,  62:  6581 
    Google Scholar
  • 5o Inagaki A. Edure S. Yatsuda S. Akita M. Chem. Commun.  2005,  5468 
    Google Scholar
  • For dyes, see:
  • 6a Hedstrand DM. Kruizinga WH. Kellogg RM. Tetrahedron Lett.  1978,  1255 
    Google Scholar
  • 6b Neumann M. Füldner S. König B. Zeitler K. Angew. Chem. Int. Ed.  2011,  50:  951 
    Google Scholar
  • 7a Sapountzis I. Knochel P. Angew. Chem. Int. Ed.  2004,  43:  897 
    Google Scholar
  • 7b Liu X. Barry M. Tsou H.-R. Tetrahedron Lett.  2007,  48:  8409 
    Google Scholar
  • 7c Enders D. Noll S. Raabe G. Runsink J. Synthesis  2008,  1288 
    Google Scholar
  • For selected reductive examples, see:
  • 8a Alonso F. Candela P. Gómez C. Yus M. Adv. Synth. Catal.  2003,  345:  275 
    Google Scholar
  • 8b Seino H. Masumori T. Hidai M. Mizobe Y. Organometallics  2003,  22:  3424 
    Google Scholar
  • 8c Sinha P. Kofink CC. Knochel P. Org. Lett.  2006,  8:  3841 
    Google Scholar
  • 8d Enders D. Funabiki K. Org. Lett.  2001,  3:  1575 
    Google Scholar
  • For selected oxidative examples, see:
  • 9a Tang Q. Zhang C. Luo M. J. Am. Chem. Soc.  2008,  130:  5840 
    Google Scholar
  • 9b Lim Y. Pang S. Paik S. Cho C. Bull. Korean Chem. Soc.  2003,  24:  543 
    Google Scholar
  • 9c Lee K. Lim Y. Cho C. Tetrahedron Lett.  2002,  43:  7463 
    Google Scholar
  • 9d Prata JV. Clemente D.-TS. Prabhakar S. Lobo AM. Mourata I. Branco PS.
    J. Chem. Soc., Perkin Trans. 1  2002,  513 
    Google Scholar
  • 9e Fernández R. Ferrete A. Llera JM. Magriz A. Martín-Zamora E. Díaz E. Lassaletta JM. Chem. Eur. J.  2004,  10:  737 
    Google Scholar
  • 10a Magnus P. Garizi N. Seibert KA. Ornholt A. Org. Lett.  2009,  11:  5646 
    Google Scholar
  • 10b Winter AH. Thomas SI. Kung AC. Falvey DE. Org. Lett.  2004,  6:  4671 
    Google Scholar
  • 11 Lebrun S. Couture A. Deniau E. Grandclaudon P. Synlett  2009,  2621 
    Article in Thieme ConnectGoogle Scholar
  • 12a Rillema DP. Allen G. Meyer TJ. Conrad D. Inorg. Chem.  1983,  22:  1617 
    Google Scholar
  • 12b Crutchley RJ. Lever ABP. J. Am. Chem. Soc.  1980,  102:  7128 
    Google Scholar
  • 15 Beeston RF. Aldridge WS. Treadway JA. Fitzgerald MC. DeGraff BA. Stitzel SE. Inorg. Chem.  1998,  37:  4368 
    CrossrefGoogle Scholar
  • 16a Neckers DC. J. Photochem. Photobiol., A  1989,  47:  1 
    Google Scholar
  • 16b Alberti MN. Vougioukalakis GC. Orfanopoulos M. J. Org. Chem.  2009,  74:  7274 
    Google Scholar
  • For selected recent reviews, see:
  • 17a Evano G. Blanchard N. Toumi M. Chem. Rev.  2008,  108:  3054 
    Google Scholar
  • 17b Ma D. Cai Q. Acc. Chem. Res.  2008,  41:  1450 
    Google Scholar
  • 17c Monnier F. Taillefer M. Angew. Chem. Int. Ed.  2009,  48:  6954 
    Google Scholar
  • 17d Surry DS. Buchwald SL. Chem. Sci.  2010,  1:  13 
    Google Scholar
  • For selected recent reviews, see:
  • 18a Hartwig JF. Acc. Chem. Res.  2008,  41:  1534 
    Google Scholar
  • 18b Surry DS. Buchwald SL. Chem. Sci.  2011,  2:  27 
    Google Scholar
  • 19a Tšubrik O. Sillard R. Mäeorg U. Synthesis  2006,  843 
    Google Scholar
  • 19b Kisseljova K. Tšubrik O. Sillard R. Mäeorg S. Mäeorg U. Org. Lett.  2006,  8:  43 
    Google Scholar
  • 20a Ishikawa S. Tsuji S. Sawaki Y. J. Am. Chem. Soc.  1991,  113:  4282 
    Google Scholar
  • 20b Harder T. Wessig P. Bendig J. Stösser R. J. Am. Chem. Soc.  1999,  121:  6580 
    Google Scholar
  • 21 Principles of Fluorescence Spectroscopy   Vol. 8:  Lakowicz JR. Springer; Berlin: 2006. 
    CrossrefGoogle Scholar
  • 22 Hu Z. Ye W. Zou H. Yu Y. Synth. Commun.  2010,  40:  222 
    CrossrefGoogle Scholar
  • 23 Tobisu M. Nakamura R. Kita Y. Chatani N. J. Am. Chem. Soc.  2009,  131:  3174 
    CrossrefGoogle Scholar
  • 24 Lusch MJ. Woller KR. Keller AM. Turk MC. Synthesis  2005,  551 
    Article in Thieme ConnectGoogle Scholar
  • 25 Moraczewski AL. Banaszynski LA. From AM. White CE. Smith BD. J. Org. Chem.  1998,  63:  7258 
    CrossrefGoogle Scholar
  • 26 Bailey WJ. Griffith JR. J. Org. Chem.  1978,  43:  2690 
    CrossrefGoogle Scholar
  • 27 Swenson RE. Sowin TJ. Zhang HQ. J. Org. Chem.  2002,  67:  9182 
    CrossrefPubMedGoogle Scholar
  • 28 Lewis FD. Wagner-Brennan JM. Miller AM. Can. J. Chem.  1999,  77:  595 
    Google Scholar
  • 29 Takács A. Jakab B. Petz A. Kollár L. Tetrahedron  2007,  63:  10372 
    CrossrefGoogle Scholar
  • 30 McKenzie WL. Foye WO. J. Med. Chem.  1972,  15:  570 
    CrossrefGoogle Scholar
  • 31 Milburn RR. Snieckus V. Angew. Chem. Int. Ed.  2004,  43:  892 
    CrossrefGoogle Scholar
  • 32 Bedford RB. Cazin CSJ. Chem. Commun.  2002,  2310 
    Google Scholar
  • 33 Kamitori Y. Hojo M. Msuda R. Yoshida T. Ohara S. Yamada K. Yoshikawa N. J. Org. Chem.  1988,  53:  519 
    CrossrefGoogle Scholar
  • 34 Mino T. Shirae Y. Sakamoto M. Fujita T. J. Org. Chem.  2005,  70:  2191 
    CrossrefGoogle Scholar
  • 35 Aylward JB. J. Chem. Soc. C  1970,  1494 
    Google Scholar
  • 36 Thu-Cuc ST. Buu-Hoi NP. Xuong ND. J. Heterocycl. Chem.  1964,  1:  28 
    CrossrefGoogle Scholar
  • 37 Desmarets C. Schneider R. Fort Y. J. Org. Chem.  2002,  67:  3029 
    Google Scholar
  • 38 Yu Y. Srogl J. Liebeskind LS. Org. Lett.  2004,  6:  2631 
    CrossrefPubMedGoogle Scholar
  • 39 Huang X. Anderson KW. Zim D. Jiang L. Klapars A. Buchwald S. J. Am. Chem. Soc.  2003,  125:  6653 
    CrossrefPubMedGoogle Scholar
  • 41 Okano K. Tokuyama H. Fukuyama T. Org. Lett.  2003,  5:  4987 
    CrossrefGoogle Scholar
  • 42 Wright WB. Brabander HJ. Hardy HA. J. Org. Chem.  1961,  26:  476 
    CrossrefGoogle Scholar
13

The abbreviation bpyrz stands for 2,2′-bipyrazine.

14

The acetylation was performed because of the volatility of N-methylaniline.

40

Commercially available. CAS number: 1019542-99-4.