PDF herunterladen
Synthesis 2013; 45(16): 2234-2240
DOI: 10.1055/s-0033-1339297
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Gram-Scale Ketone Synthesis by Direct Reductive Coupling of Alkyl Iodides with Acid Chlorides

Wenbin Lu
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   eMail: hegui_gong@shu.edu.cn
,
Zhuye Liang
b   College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Science Road, Zhengzhou 450001, P. R. of China
,
Yuwei Zhang
b   College of Chemistry and Molecular Engineering, Zhengzhou University, 100 Science Road, Zhengzhou 450001, P. R. of China
,
Fan Wu
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   eMail: hegui_gong@shu.edu.cn
,
Qun Qian*
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   eMail: hegui_gong@shu.edu.cn
,
Hegui Gong*
a   Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China   Fax: +86(21)66132410   eMail: hegui_gong@shu.edu.cn
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 30. April 2013

Accepted after revision: 06. Juni 2013

Publikationsdatum:
11. Juli 2013 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

Alkyl aryl ketones were prepared on a gram scale by the nickel-catalyzed reductive coupling of alkyl iodides with aroyl chlorides. When scaled up 30-fold, this reaction shows a comparable coupling efficiency to the previously reported reaction performed under small-scale conditions. The mild and convenient reaction conditions show excellent tolerance to a range of functional groups and provide the ketones in good to excellent yields.

Key words

nickel - catalysis - ketones - halides - reductions
 

  • References

  • 1 These authors contributed equally to the work.

      • For reviews and selected examples, see:
    • 2a Johnson JB, Rovis T. Acc. Chem. Res. 2008; 41: 327
      Crossref
    • 2b Tamaru Y, Ochiai H, Nakamura T, Yoshida Z. Angew. Chem., Int. Ed. Engl. 1987; 26: 1157
      Crossref
    • 2c Reddy CK, Knochel P. Angew. Chem., Int. Ed. Engl. 1996; 35: 1700
      Crossref
  • 3 Wu F, Lu W, Qian Q, Ren Q, Gong H. Org. Lett. 2012; 14: 3044
    CrossrefPubMed
  • 4 Yin H, Zhao C, You H, Lin K, Gong H. Chem. Commun. 2012; 48: 7034
    CrossrefPubMed

      • For notable similar works on the coupling of alkyl halides with alkanoic acid derivatives, see:
    • 5a Wotal AC, Weix DJ. Org. Lett. 2012; 14: 1476
      CrossrefPubMed
    • 5b d’Incan E, Sibille S, Périchon J, Moingeon M.-O, Chaussard J. Tetrahedron Lett. 1986; 27: 4175
      Crossref
    • 5c Onaka M, Matsuoka Y, Mukaiyama T. Chem. Lett. 1981; 10: 531
  • 6 Steib AK, Thaler T, Komeyama K, Mayer P, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 3303
    Crossref
  • 7 Cai L, Zhao H, Zhang W, Dai L. WO 2010127574, 2010