Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Electrochemical Properties and Regioselectivity of Cyclopalladation of Chiral Ferrocenylimines Deriving from (S)-Ferrocenylethylamine

Zhigang Yin A C , Hengyu Qian A , Quanling Wang A , Huichao Dong A , Shihai Yan B C , Chunxia Zhang A and Junhua Li A
+ Author Affiliations
- Author Affiliations

A Key Laboratory of Surface & Interface Science of Henan, School of Material & Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, China.

B Lab of Biofuel, Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China.

C Corresponding authors. Email: yinck2010@yahoo.com.cn; yansh@qibebt.ac.cn

Australian Journal of Chemistry 66(2) 218-226 https://doi.org/10.1071/CH12367
Submitted: 3 August 2012  Accepted: 19 October 2012   Published: 12 December 2012

Abstract

Treatment of a cyclopalladated complex derived from chiral ferrocenylimine (η5-C5H5)Fe(η5-C5H4)–CH(CH3)–N=CH–2-C4H3S, (Sc)-1, with PPh3 produced the heteroannular palladacycle (Sc)-3 in which palladation occurred at the unsubstituted cyclopentadiene ring. While for (η5-C5H5)Fe(η5-C5H4)–CH(CH3)–N=CH–C6H5, (Sc)-4, cyclopalladation took place mainly at the phenyl ring; the heteroannular palladacycle (Sc)-6, as a minor product, was also obtained. Single crystal X-ray analysis, electrochemical, and computational studies have been performed, showing good agreement with experimental results.


References

[1]  L. Ackermann, Chem. Rev. 2011, 111, 1315.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXivVSgt7k%3D&md5=96e1836656d681ceeaf32bc828d8516bCAS |

[2]  T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmslWksQ%3D%3D&md5=903df50b68782b533f9f0a2ab206dbefCAS |

[3]  J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksVWjsbY%3D&md5=28ec02f1875fbfd9fcd4d63ae5c1cb22CAS |

[4]  A. D. Ryabov, Chem. Rev. 1990, 90, 403.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXhtl2jtL0%3D&md5=204f9845c512507a0e74defafb8fe373CAS |

[5]  V. V. Dunina, O. A. Zalevskaya, V. M. Potapov, Russ. Chem. Rev. 1988, 57, 250.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  A. C. Cope, R. W. Siekman, J. Am. Chem. Soc. 1965, 87, 3272.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2MXks1ehtbg%3D&md5=75bb41acfcec76deae9f44e3e98fdbd7CAS |

[7]  A. C. Cope, E. C. Friedrich, J. Am. Chem. Soc. 1968, 90, 909.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXkt1Oms78%3D&md5=ec5f22172e1ee579893c599c66c3c3b8CAS |

[8]  M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjs1KktA%3D%3D&md5=12379aa8ced1c753bd951ec823129252CAS |

[9]  R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhvVWjtbc%3D&md5=4782923914de20887498b9fcca08f487CAS |

[10]  G. K. Rao, A. Kumar, J. Ahmed, A. K. Singh, Chem. Commun. 2010, 46, 5954.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXpslWiu7w%3D&md5=d04eb5d8ebdb2fccd62073e686db54caCAS |

[11]  D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2010, 132, 3965.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXit1CltLo%3D&md5=4677554e3f829700dae9c38608dcb30cCAS |

[12]  E. M. Beccalli, E. Borsini, S. Brenna, S. Galli, M. Rigamonti, G. Broggini, Chemistry 2010, 16, 1670.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVKjs7k%3D&md5=b16e7648b0510a9f07daf0eaa188333aCAS |

[13]  V. V. Dunina, O. N. Gorunova, Russ. Chem. Rev. 2005, 74, 871.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht12rsLs%3D&md5=5234494e16b5458ca2d465c51143e07eCAS |

[14]  S. Jautze, P. Seiler, R. Peters, Angew. Chem. Int. Ed. 2007, 46, 1260.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXit1Sju70%3D&md5=e785d7719beba49d8d607c4808ba3e00CAS |

[15]  A. Molnár, Chem. Rev. 2011, 111, 2251.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  V. V. Dunina, O. N. Gorunova, P. A. Zykov, K. A. Kochetkov, Russ. Chem. Rev. 2011, 80, 51.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXltF2lurc%3D&md5=4a678aeb2f554ecc9ef96be4acf67fc8CAS |

[17]  S. Lentijo, J. A Miguel, P. Espinet, Dalton Trans. 2011, 40, 7602.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXos1Gltbk%3D&md5=4b331d24aa236b482359a0bb089b22acCAS |

[18]  D. A. Alonso, C. Nájera, Chem. Soc. Rev. 2010, 39, 2891.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptFyhu78%3D&md5=8dfbd2d3616ae0170f9cf70c152f3398CAS |

[19]  C. R. Oliveira, C. M. V. Barbosa, F. D. Nascimento, C. S. Lanetzki, M. B. Meneghin, F. E. G. Pereira, E. J. Paredes-Gamero, A. T. Ferreira, T. Rodrigues, M. L. S. Queiroz, A. C. F. Caires, I. L. S. Tersariol, C. Bincoletto, Chem. Biol. Interact. 2009, 177, 181.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFeltb4%3D&md5=094a792ace7741e99183d4cd0baa239fCAS |

[20]  N. D. Wang, J. Xiang, Z. B. Ma, J. M. Quan, J. H. Chen, Z. Wang, J. Comb. Chem. 2008, 10, 825.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVChsLrN&md5=7f2cc4255c48108b5ff549bde62af3c9CAS |

[21]  A. Gómez-Quiroga, C. Navarro-Ranninger, Coord. Chem. Rev. 2004, 248, 119.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  A. Moyano, R. Rios, Synlett 2009, 1863.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpvFGmtrY%3D&md5=2b43bce8f0d693e91f62b9302f054880CAS |

[23]  C. Xu, Z. Q. Wang, W. J. Fu, X. H. Lou, Y. F. Li, F. F. Cen, H. J. Ma, B. M. Ji, Organometallics 2009, 28, 1909.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvFGnsLo%3D&md5=438e7a5b399934969c43225ade340315CAS |

[24]  A. González, C. López, X. Solans, M. Font-Bardía, E. Molins, J. Organomet. Chem. 2008, 693, 2119.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  R. Peters, Z. Xin, D. F. Fischer, W. B. Schweizer, Organometallics 2006, 25, 2917.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjvFKqs74%3D&md5=5423e087922fedc0eac779b015eccafeCAS |

[26]  G. Zhao, Q. C. Wang, T. C. W. Mark, J. Chem. Soc., Dalton Trans. 1998, 3785.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXnvFCktLg%3D&md5=1ba87aa0d2244e35ce499c4159201354CAS |

[27]  A. Moyano, M. Rosol, R. M. Moreno, C. López, M. A. Maestro, Angew. Chem. Int. Ed. 2005, 44, 1865.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXislWrsbg%3D&md5=f3db5855836f6ce2cef25ade81ba94a0CAS |

[28]  L. L. Troitskaya, Z. A. Starikova, T. V. Demeshchik, S. T. Ovseenko, E. V. Vorontsov, V. I. Sokolov, J. Organomet. Chem. 2005, 690, 3976.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpt1ajur4%3D&md5=869b5c1ab4d0f50fc60d5965d28b15beCAS |

[29]  H. Y. Qian, X. L. Cui, M. S. Tang, C. H. Liu, C. Liu, Y. J. Wu, New J. Chem. 2009, 33, 668.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXislOjsbg%3D&md5=e0f339d014a369e39e5c545808177356CAS |

[30]  X. M. Zhao, X. Q. Hao, B. Liu, M. L. Zhang, M. P. Song, Y. J. Wu, J. Organomet. Chem. 2006, 691, 255.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlSjtL%2FM&md5=feaffa0aec387accc244e1d9a55b1ab6CAS |

[31]  I. Omae, Coord. Chem. Rev. 2004, 248, 995.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnt12qur0%3D&md5=50a328fbab0f7853dbdcc0f68038cb0eCAS |

[32]  R. Bosque, C. López, J. Sales, D. Tramuns, X. Solans, Dalton Trans. 1995, 2445.
         | 1:CAS:528:DyaK2MXnt1ait74%3D&md5=c0b7611fdf7ce59c5bb999c34d37e1d0CAS |

[33]  M. Gómez, J. Granell, M. Martinez, Organometallics 1997, 16, 2539.
         | Crossref | GoogleScholarGoogle Scholar |

[34]  C. López, J. Sales, X. Solans, R. Zquiak, J. Chem. Soc., Dalton Trans. 1992, 2321.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  J. Albert, M. Gómez, J. Granell, J. Sales, Organometallics 1990, 9, 1405.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXitFOhsLg%3D&md5=1a6fcf9b8bacd7f5aad44e70ba4bf019CAS |

[36]  L. Pauling, The Nature of the Chemical Bond, Third Edn. 1960 (Cornell University Press: New York, NY).

[37]  R. Bosque, C. López, J. Sales, Inorg. Chim. Acta 1996, 244, 141.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhvVKlu78%3D&md5=126bbbfb169c3b55f1b6d305a245edbfCAS |

[38]  M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03 2004 (Gaussian, Inc.: Wallingford, CT).

[39]  M. Benito, C. López, X. Morvan, Polyhedron 1999, 18, 2583.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmsFCit78%3D&md5=40db3c3666c86208d1d1806bf2487604CAS |

[40]  I. Omae, Coord. Chem. Rev. 2004, 248, 995.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnt12qur0%3D&md5=50a328fbab0f7853dbdcc0f68038cb0eCAS |

[41]  G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures 1997 (University of Göttingen: Germany).