Synthesis 2014; 46(14): 1881-1885
DOI: 10.1055/s-0033-1339119
special topic
© Georg Thieme Verlag Stuttgart · New York

Carboxylation of Organoboronic Esters with Potassium Methyl Carbonate under Copper Catalysis

Hung A. Duong*
Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros #07-01, Singapore 138665, Singapore   Fax: +65(646)42102   Email: duong_hung@ices.a-star.edu.sg   Email: nguyen_minh@ices.a-star.edu.sg
,
Tuan Minh Nguyen*
Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros #07-01, Singapore 138665, Singapore   Fax: +65(646)42102   Email: duong_hung@ices.a-star.edu.sg   Email: nguyen_minh@ices.a-star.edu.sg
,
Nurul Zubaidah Binte Rosman
Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros #07-01, Singapore 138665, Singapore   Fax: +65(646)42102   Email: duong_hung@ices.a-star.edu.sg   Email: nguyen_minh@ices.a-star.edu.sg
,
Lionel Jia Liang Tan
Organic Chemistry, Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), 8 Biomedical Grove, Neuros #07-01, Singapore 138665, Singapore   Fax: +65(646)42102   Email: duong_hung@ices.a-star.edu.sg   Email: nguyen_minh@ices.a-star.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 20 February 2014

Accepted: 14 April 2014

Publication Date:
02 June 2014 (eFirst)

Abstract

In the presence of a copper catalyst, potassium methyl carbonate serves as a versatile carboxylating agent of allyl- and ­arylboronic esters for the preparation of carboxylic acids.

Supporting Information

 
  • References

    • 1a Mechoulam R, Ben-Zvi Z. Chem. Commun. 1969; 343
    • 1b Stiles M, Finkbeiner HL. J. Am. Chem. Soc. 1959; 81: 505
    • 1c Stiles M. J. Am. Chem. Soc. 1969; 81: 2598
    • 1d Isaacs RC. A, Di Grandi MJ, Danishefsky SJ. J. Org. Chem. 1993; 58: 3938
    • 1e Finkbeiner H. J. Am. Chem. Soc. 1964; 86: 961
  • 2 Ohishi T, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2008; 47: 5792
  • 3 Duong HA, Huleatt PB, Tan Q.-W, Lau ES. Org. Lett. 2013; 14: 4034
    • 4a Behrendt W, Gattow G, Draeger M. Z. Anorg. Allg. Chem. 1973; 397: 237
    • 4b Stueber D, Patterson D, Mayne CL, Orendt AM, Grant DM, Parry RW. Inorg. Chem. 2001; 40: 1902
  • 5 Ukai K, Aoki M, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2006; 128: 8706
  • 7 These compounds are commercially available.