Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(14): 1881-1885
DOI: 10.1055/s-0033-1339119
DOI: 10.1055/s-0033-1339119
special topic
Carboxylation of Organoboronic Esters with Potassium Methyl Carbonate under Copper Catalysis
Further Information
Publication History
Received: 20 February 2014
Accepted: 14 April 2014
Publication Date:
02 June 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201414/lookinside/thumbnails/10.1055-s-0033-1339119-1.jpg)
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
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- 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
- 6a Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
- 6b Ishiyama T, Itoh Y, Kitano T, Miyaura N. Tetrahedron Lett. 1997; 38: 3447
- 6c Ishiyama T, Ishida K, Miyaura N. Tetrahedron 2001; 57: 9813
- 6d Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
- 6e Hall DG In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials. 2nd ed. Wiley-VCH; Weinheim: 2011
- 7 These compounds are commercially available.
For selected references, see: