Synthesis 2014; 46(03): 290-294
DOI: 10.1055/s-0033-1340106
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1,2-Dimetallic Compounds via Direct Insertion of Zinc Powder in the Presence of InCl3: Synthesis of ortho-Bis-functionalized Aromatics

Thomas Klatt
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
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Tobias D. Blümke
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
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Maximilian A. Ganiek
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
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Paul Knochel*
Ludwigs-Maximilians-Universität München, Department Chemie, Butenandtstraße 5-13, Haus F, 81377 München, Germany   Fax: +49(89)218077680   Email: Paul.Knochel@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 10 October 2013

Accepted: 14 October 2013

Publication Date:
13 November 2013 (online)


Abstract

A variety of functionalized 1,2-dizinc reagents can be prepared by an indium-catalyzed insertion of zinc powder into aromatic 1,2-dibromides or 1-bromo-2-triflates. These 1,2-dimetallics undergo Cu- or Pd-catalyzed acylations, allylations, or cross couplings.

Supporting Information

 
  • References

    • 1a Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
    • 1b Knochel P, Millot N, Rodriguez A, Tucker CE. Org. React. 2001; 58: 417
    • 1c Knochel P In Handbook of Functionalized Organometallics . Wiley-VCH; Weinheim: 2005
    • 2a Negishi E, King AO, Okukado N. J. Org. Chem. 1977; 42: 1821
    • 2b Negishi E, Valente LF, Kobayashi M. J. Am. Chem. Soc. 1980; 102: 3298
    • 2c Wang G, Yin N, Negishi E. Chem. Eur. J. 2011; 17: 4118
    • 2d Negishi E, Zeng X, Tan Z, Qian M, Hu Q, Huang Z In Metal-Catalyzed Cross-Coupling Reactions . 2nd ed.; de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004: 815-877
    • 3a Milne JE, Buchwald SL. J. Am. Chem. Soc. 2004; 126: 13028
    • 3b Han C, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 7532
    • 3c Çalimsiz S, Sayah M, Mallik D, Organ MG. Angew. Chem. Int. Ed. 2010; 49: 2014
    • 3d Hadei N, Achonduh GT, Valente C, O’Brien J, Organ MG. Angew. Chem. Int. Ed. 2011; 50: 3896
  • 4 Krasovksiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040
  • 5 Metzger A, Schade MA, Knochel P. Org. Lett. 2008; 10: 1107
    • 6a Takai K, Ikawa Y. Org. Lett. 2002; 4: 1727
    • 6b Takai K, Ueda T, Hayashi T, Moriwake T. Tetrahedron Lett. 1996; 37: 7049
    • 7a Blümke TD, Chen Y.-H, Peng Z, Knochel P. Nat. Chem. 2010; 2: 313
    • 7b Blümke TD, Peng Z, Mayer P, Knochel P. Angew. Chem. Int. Ed. 2010; 49: 8516
    • 7c Blümke TD, Groll K, Karaghiosoff K, Knochel P. Org. Lett. 2011; 13: 6440
    • 7d Uneyama K, Kamaki N, Moriya A, Torii S. J. Org. Chem. 1985; 50: 5396
    • 7e Tanaka H, Nakahara T, Dhimane H, Torii S. Tetrahedron Lett. 1989; 30: 4161
    • 7f Tanaka H, Inoue K, Pokorski U, Taniguchi M, Torii S. Tetrahedron Lett. 1990; 31: 3023
    • 7g Saito S In Science of Synthesis . Vol. 7. Yamamoto H. Georg Thieme Verlag; Stuttgart: 2004: 5
  • 8 Blümke TD, Klatt T, Koszinowski K, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9926
  • 9 The yield was determined by GC analysis of iodolyzed reaction aliquots in THF
    • 10a Organ MG, Calimsiz S, Sayah M, Hoi KH, Lough AJ. Angew. Chem. Int. Ed. 2009; 48: 2383
    • 10b O’Brien CJ, Kantchev EA. B, Valente C, Hadei N, Chass GA, Lough A, Hopkins AC, Organ MG. Chem. Eur. J. 2006; 12: 4743
    • 10c Nasielski J, Hadei N, Achonduh G, Kantchev EA. B, O’Brien CJ, Lough A, Organ MG. Chem. Eur. J. 2010; 16: 10844
  • 11 Knochel P, Yeh MC. P, Berk SC, Talbert J. J. Org. Chem. 1988; 53: 2390