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

Halomethyllithium Carbenoids: Versatile Reagents for the Homologation of Electrophilic Carbon Units

Vittorio Pace A
+ Author Affiliations
- Author Affiliations

A Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria. Email: vpace@farm.ucm.es




Vittorio Pace received a degree in Pharmacy from the University of Perugia (Italy) in 2005 and an MSc in Drug Design and Development from the University of Pavia (Italy) in 2008. He obtained a PhD in Chemistry under the guidance of Professor A. R. Alcántara at the Complutense University of Madrid (2010). He then undertook postdoctoral training at the University of Vienna (Austria) with Professor W. Holzer and at the University of Manchester (UK) with Professor D. J. Procter. In October 2013, he moved to the University of Stockholm (Sweden) for a third postdoctoral position with Professor B. Olofsson.

Australian Journal of Chemistry 67(2) 311-313 https://doi.org/10.1071/CH13416
Submitted: 10 August 2013  Accepted: 17 October 2013   Published: 28 November 2013


References

[1]  M. Braun, in The Chemistry of Organolithium Compounds (Eds Z. Rappoport, I. Marek) 2004, Vol. 2, pp. 829–899 (Wiley-VCH: Chichester).

[2]  G. L. Closs, R. A. Moss, J. Am. Chem. Soc. 1964, 86, 4042.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXkslKhsLw%3D&md5=eb71e632dd1d19a536347097a8482873CAS |

[3]  V. Capriati, S. Florio, Chem. Eur. J. 2010, 16, 4152.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXks12qurc%3D&md5=f59a491b54af3702b76ded0054530e15CAS | 20222089PubMed |

[4]     (a) H. Siegel, in Topics in Current Chemistry, Vol. 106 1982, pp. 55–78 (Springer: Heidelberg).
      (b) H. Hermann, J. C. W. Lohrenz, A. Kühn, G. Boche, Tetrahedron 2000, 56, 4109.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  G. Köbrich, A. Akhtar, F. Ansari, W. E. Breckoff, H. Büttner, W. Drischel, R. H. Fischer, K. Flory, H. Fröhlich, W. Goyert, H. Heinemann, I. Hornke, H. R. Merkle, H. Trapp, W. Zündorf, Angew. Chem. Int. Ed. Engl. 1967, 6, 41.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) G. Maas, Angew. Chem. Int. Ed. 2009, 48, 8186.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht12htLjJ&md5=ab35aa6c7001f72d38e59b7ecee8b9e9CAS |
      (b) V. Pace, G. Verniest, J. V. Sinisterra, A. R. Alcántara, N. De Kimpe, J. Org. Chem. 2010, 75, 5760.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1962, 84, 867.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF38XktVelt7w%3D&md5=2b5d3c8ad12ed08ba0b8c5f5ac7257ebCAS |

[8]  G. Boche, J. C. W. Lohrenz, Chem. Rev. 2001, 101, 697.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhtl2ksbs%3D&md5=e63285870e47c01670c9da3c90e0c515CAS | 11712501PubMed |

[9]  K. M. Sadhu, D. S. Matteson, Tetrahedron Lett. 1986, 27, 795.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXhvValtw%3D%3D&md5=b51fcee7f94dddf2fc58946e53794cbaCAS |

[10]  V. Pace, W. Holzer, G. Verniest, A. R. Alcántara, N. De Kimpe, Adv. Synth. Catal. 2013, 355, 919.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXjtlaqs7o%3D&md5=bb82a56746e58628437b1e751426aae2CAS |

[11]  D. C. Kapeller, F. Hammerschmidt, J. Am. Chem. Soc. 2008, 130, 2329.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXps1KgtQ%3D%3D&md5=0be2f83254e864820c05b94f17bcf8ecCAS | 18217759PubMed |

[12]  R. Tarhouni, B. Kirschleger, M. Rambaud, J. Villieras, Tetrahedron Lett. 1984, 25, 835.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXlslWgsrc%3D&md5=5a283e4cfd72ba6669bd210a91cededcCAS |

[13]  J. Barluenga, J. M. Fernández-Simón, J. M. Concellón, M. Yus, J. Chem. Soc., Perkin Trans. 1 1989, 77.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXktl2is78%3D&md5=82863caef560db4d9f2674168f927516CAS |

[14]  (a) J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett. 2008, 10, 4457.
         | Crossref | GoogleScholarGoogle Scholar | 18788813PubMed |
      (b) J. M. Concellón, H. Rodríguez-Solla, P. L. Bernad, C. Simal, J. Org. Chem. 2009, 74, 2452.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  V. Pace, L. Castoldi, W. Holzer, Chem. Commun. 2013, 8383.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtlakurjK&md5=7de8628bfcef602a7e59beab1ffc3d2fCAS |

[16]  (a) K. Izawa, T. Onishi, Chem. Rev. 2006, 106, 2811.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XivVemu7w%3D&md5=9c986d095c7f216e437a64494e4a9e7aCAS | 16836300PubMed |
      (b) V. Pace, L. Castoldi, M. Pregnolato, Mini Rev. Med. Chem. 2013, 13, 988.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  J. Barluenga, B. Baragaña, J. M. Concellón, J. Org. Chem. 1995, 60, 6696.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXotleltrw%3D&md5=51f92a6288e40c07bb1a4c79ce73d7d0CAS |

[18]  (a) T. Onishi, N. Hirose, T. Nakano, M. Nakazawa, K. Izawa, Tetrahedron Lett. 2001, 42, 5883.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXlsFOlu7s%3D&md5=a90a68001ed26fc0e3539d8810cd82c5CAS |
      (b) T. Onishi, T. Nakano, N. Hirose, M. Nakazawa, K. Izawa, Tetrahedron Lett. 2001, 42, 5887.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  (a) S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XosFSitg%3D%3D&md5=e58ef66b56c5cd5ce272cf2920f7c3bcCAS |
      (b) S. Balasubramaniam, I. S. Aidhen, Synthesis 2008, 3707.
      (c) V. Pace, L. Castoldi, A. R. Alcantara, W. Holzer, RSC Adv. 2013, 3, 10158.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  (a) V. Pace, L. Castoldi, M. J. Hernáiz, A. R. Alcántara, W. Holzer, Tetrahedron Lett. 2013, 54, 4369.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVCrtbbK&md5=0996cfb3ea97340c1d359bab258a8c29CAS |
      (b) V. Pace, W. Holzer, Tetrahedron Lett. 2012, 53, 5106.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) V. Pace, Á. Cortés-Cabrera, V. Ferrario, J. V. Sinisterra, C. Ebert, L. Gardossi, P. Braiuca, A. R. Alcántara, J. Mol. Catal., B Enzym. 2011, 70, 23.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) V. Pace, Á. Cortés-Cabrera, M. Fernández, J. V. Sinisterra, A. R. Alcántara, Synthesis 2010, 3545.
      (e) V. Pace, Synlett 2010, 2825.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) V. Pace, F. Martínez, M. Fernández, J. V. Sinisterra, A. R. Alcántara, Adv. Synth. Catal. 2009, 351, 3199.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  V. Pace, L. Castoldi, W. Holzer, J. Org. Chem. 2013, 78, 7764.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVWhtb%2FM&md5=15a2102e9ac24958158b4c1c1f2e3889CAS | 23805887PubMed |

[22]  E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1964, 86, 1640.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXktVCjsrw%3D&md5=e30cf96c297c087177df1c368915055eCAS |