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 2018; 50(10): 2119-2123
DOI: 10.1055/s-0036-1591912
DOI: 10.1055/s-0036-1591912
paper
One-Step O-Demethyl-Decarboxylation of ortho-Methoxy Aromatic Carboxylic Acids
We thank the CNRS for its financial support, the Ministère de l’Education Nationale et de la Recherche for a grant to M.P. and M2i company for a grant to E.Z.Further Information
Publication History
Received: 26 December 2017
Accepted: 29 December 2017
Publication Date:
03 April 2018 (online)

Abstract
A highly selective decarboxydemethylation of o-methoxyarenecarboxylic acids is described. The reaction takes place in DMPU at 170 °C in the presence of TMEDA and iron powder. A similar reaction has not been reported until now.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591912.
- Supporting Information
-
References
- 1a Fager EW. J. Am. Chem. Soc. 1945; 67: 2217
- 1b Turnbull SG. Jr. US Patent 2453103, 1948
- 1c Cairncross A. Roland JR. Henderson RM. Sheppard WA. J. Am. Chem. Soc. 1970; 92: 3187
- 1d Cohen T. Schambach RA. J. Am. Chem. Soc. 1970; 92: 3189
- 1e Cohen T. Berninger RW. Wood JT. J. Org. Chem. 1978; 43: 837
- 1f Nilsson M. Acta Chem. Scand. 1966; 20: 423
- 1g Björklung C. Nilsson M. Acta Chem. Scand. 1968; 22: 2585
- 1h Chodowska-Palicka J. Nilsson M. Acta Chem. Scand. 1970; 24: 3353
- 1i Nilsson M. Ullenius C. Acta Chem. Scand. 1971; 25: 2428
- 1j Chodowska-Palicka J. Nilsson M. Acta Chem. Scand. 1971; 25: 3451
- 1k Shepard AF. Winslow NR. Johnson JR. J. Am. Chem. Soc. 1930; 52: 2083
- 1l Shang R. Liu L. Sci. China: Chem. 2011; 54: 1670
- 1m Goossen LJ. Rodriguez N. Goossen K. Angew. Chem. Int. Ed. 2008; 47: 3100
- 1n Goossen LJ. Goossen K. Rodriguez N. Blanchot M. Linder C. Zimmermann B. Pure Appl. Chem. 2008; 80: 1725
- 1o Goossen LJ. Deng G. Levy LM. Science 2006; 313: 662
- 1p Goossen LJ. Thiel WR. Rodriguez N. Linder C. Melzer B. Adv. Synth. Catal. 2007; 349: 2241
- 1q Goossen LJ. Melzer B. J. Org. Chem. 2007; 72: 7473
- 1r Goossen LJ. Rodriguez N. Melzer B. Linder C. Deng G. Levy LM. J. Am. Chem. Soc. 2007; 129: 4824
- 1s Goossen LJ. Rodriguez N. Linder C. J. Am. Chem. Soc. 2008; 130: 15248
- 1t Goossen LJ. Rodriguez N. Lange PP. Linder C. Angew. Chem. Int. Ed. 2010; 49: 1111
- 1u Shang R. Fu Y. Wang Y. Xu Q. Yu H.-Z. Liu L. Angew. Chem. Int. Ed. 2009; 48: 9350
- 2a Goossen LJ. Linder C. Rodriguez N. Lange PP. Fromm A. Chem. Commun. 2009; 7173
- 2b Cornella J. Sanchez C. Banawa D. Larrosa I. Chem. Commun. 2009; 7176
- 2c Goossen LJ. Rodriguez N. Linder C. Lange PP. Fromm A. ChemCatChem 2010; 2: 430
- 2d Xue L. Su W. Lin Z. Dalton Trans. 2011; 40: 11926
- 2e Dickstein JS. Mulrooney CA. O’Brien EM. Morgan BJ. Kozlowski MC. Org. Lett. 2007; 9: 2441
- 2f Sun Z.-M. Zhao P. Angew. Chem. Int. Ed. 2009; 48: 6726
- 3 Cahiez G. Moyeux A. Gager O. Poizat M. Adv. Synth. Catal. 2013; 355: 790
- 4a Grobelny Z. Eur. J. Org. Chem. 2004; 14: 2973
- 4b Maercker A. Angew. Chem. Int. Ed. 1987; 26: 972
- 4c Bhatt MV. Kulkarni SU. Synthesis 1983; 249
- 5a Tezuka T. Yamashita Y. Mukai T. J. Am. Chem. Soc. 1976; 98: 6051
- 5b Dean FM. Goodchild J. Houghton LE. Martin JA. Morton RB. Parton B. Price AW. Somvichien N. Tetrahedron Lett. 1966; 7: 4153
- 5c McOmie JF. W. Watts ML. West DE. Tetrahedron 1968; 24: 2289
- 6 Feutrill GI. Mirrington RN. Tetrahedron Lett. 1970; 11: 1327
- 7a Rubio M. Hernandez AG. Daudey JP. Cetina R. J. Org. Chem. 1980; 45: 150
- 7b Li Z.-H. Wang W.-N. Fan K.-N. Wong MW. Huang H.-H. Huang W. Chem. Phys. Lett. 1999; 305: 474
- 8a Tsuji J. Ohno K. Synthesis 1969; 157
- 8b Maetani S. Fukuyama T. Suzuki N. Idshihara D. Ryu I. Chem. Commun. 2012; 48: 2552
- 9 Trovitch RJ. Lobkovsky E. Bouwkamp MW. Chirik PJ. Organometallics 2008; 27: 6264
- 10 Abraham RJ. Reid M. J. Chem. Soc., Perkin Trans. 2 2002; 1081
- 11 Gozzo FC. Fernandes SA. Rodrigues DC. Eberlin MN. Marsaioli AJ. J. Org. Chem. 2003; 68: 5493
- 12 Naidu AB. Jaseer EA. Sekar G. J. Org. Chem. 2009; 74: 3675
- 13 Song LX. Wang HM. Yang Y. Xu P. Bull. Chem. Soc. Jpn. 2007; 80: 2185
- 14a For 1H NMR, see: Kasthuralah M. Kumar KA. Reddy CS. J. Heterocycl. Chem. 2004; 41: 413
- 14b For 13C NMR, see: Shapiro MJ. J. Org. Chem. 1978; 43: 212
- 15 Bovonsombat P. Ali R. Khan C. Leykajarakul J. Pla-on K. Aphimanchindakul S. Pungcharoenpong N. Timsuea N. Aruntat A. Punpongjareorn N. Tetrahedron 2010; 66: 6928
- 16 Furuya T. Kaiser HM. Ritter T. Angew. Chem. Int. Ed. 2008; 47: 5993
- 17a For 1H NMR, see: Motoyama Y. Kamo K. Nagashima H. Org. Lett. 2009; 11: 1345
- 17b For 13C NMR, see: Ramesh R. Bhat RG. Chandrasekaran S. J. Org. Chem. 2005; 70: 837
For selected references on Cu-mediated decarboxylation of aromatic carboxylic acids, see:
For selected references on Ag-, Pd-, and Rh-catalyzed decarboxylation of aromatic carboxylic acids, see:
For reviews, see: