Facile, One‐Pot, and Gram‐Scale Synthesis of 3,4,5‐Triiodoanisole through a C–H Iodination/ipso‐Iododecarboxylation Strategy: Potential Application towards 3,4,5‐Trisubstituted Anisoles

作者: Raed M. Al-Zoubi , Hussein Al-Mughaid , Mariam A. Al-Zoubi , Khaled T. Jaradat , Robert McDonald

DOI: 10.1002/EJOC.201500887

关键词:

摘要: A facile, efficient, and gram-scale method for the conversion of para-anisic acid into 3,4,5-triiodoanisole through a one-pot C–H iodination/ipso-iododecarboxylation reaction was investigated. Commercially available benzoic used, which allowed to be performed on multigram scale in good yield. This report discloses practical synthesis hitherto unknown that is catalytic, scalable, easy work up purify. Potential application target compound as precursor novel site-selective metal–iodine exchange Suzuki–Miyaura cross-coupling reactions were also explored. 3,4,5-Trisubstituted anisole derivatives provided highly regioselective fashion; these compounds are useful building blocks indeed hard prepare by any other means.

参考文章(98)
Warren W. Kaeding, G. Robert Collins, Oxidation of Aromatic Acids. V. Preparation of Salicylic Acids from Benzoic Acids Journal of Organic Chemistry. ,vol. 30, pp. 3750- 3754 ,(1965) , 10.1021/JO01022A036
Tetsuya Satoh, Masahiro Miura, Transition-Metal-CatalyzedRegioselective Arylation and Vinylation of CarboxylicAcids Synthesis. ,vol. 2010, pp. 3395- 3409 ,(2010) , 10.1055/S-0030-1258225
Daniell Lewis Mattern, Direct Aromatic Periodination Journal of Organic Chemistry. ,vol. 49, pp. 3051- 3053 ,(1984) , 10.1021/JO00191A003
Zhentao Wang, Lin Zhu, Feng Yin, Zhongquan Su, Zhaodong Li, Chaozhong Li, Silver-Catalyzed Decarboxylative Chlorination of Aliphatic Carboxylic Acids Journal of the American Chemical Society. ,vol. 134, pp. 4258- 4263 ,(2012) , 10.1021/JA210361Z
Bernard Bennetau, Jacques Mortier, Jo�l Moyroud, Jean-Luc Guesnet, Directed lithiation of unprotected benzoic acids Journal of The Chemical Society-perkin Transactions 1. pp. 1265- 1271 ,(1995) , 10.1039/P19950001265
J. I. Concepcion, C. G. Francisco, R. Freire, R. Hernandez, J. A. Salazar, E. Suarez, Iodosobenzene diacetate, an efficient reagent for the oxidative decarboxylation of carboxylic acids Journal of Organic Chemistry. ,vol. 51, pp. 402- 404 ,(1986) , 10.1021/JO00353A026
H. Hunsdiecker, Cl. Hunsdiecker, Über den Abbau der Salze aliphatischer Säuren durch Brom Berichte der deutschen chemischen Gesellschaft (A and B Series). ,vol. 75, pp. 291- 297 ,(1942) , 10.1002/CBER.19420750309
E. B. Merkushev, Advances in the synthesis of iodoaromatic compounds Synthesis. ,vol. 1988, pp. 923- 937 ,(1988) , 10.1055/S-1988-27758