Iodine promoted α-hydroxylation of ketones

作者: Yogesh Siddaraju , Kandikere Ramaiah Prabhu

DOI: 10.1039/C5OB00684H

关键词: Organic chemistryChemistryα hydroxylationArylIodine

摘要: A novel method for α-hydroxylation of ketones using substoichiometric amount iodine under metal-free conditions is described. This has been successfully employed in synthesizing a variety heterocyclic compounds, which are useful precursors. α-Hydroxylation diketones and triketones illustrated. strategy provides novel, efficient, mild inexpensive aryl sub-stoichiometric molecular iodine.

参考文章(34)
Muhammet Uyanik, Daisuke Suzuki, Takeshi Yasui, Kazuaki Ishihara, In situ generated (hypo)iodite catalysts for the direct α-oxyacylation of carbonyl compounds with carboxylic acids. Angewandte Chemie. ,vol. 50, pp. 5331- 5334 ,(2011) , 10.1002/ANIE.201101522
Kaliyamoorthy Alagiri, Pradeep Devadig, Kandikere R. Prabhu, CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions. Chemistry: A European Journal. ,vol. 18, pp. 5160- 5164 ,(2012) , 10.1002/CHEM.201200100
Manjunath Lamani, Kandikere Ramaiah Prabhu, Iodine-Catalyzed Amination of Benzoxazoles: A Metal-Free Route to 2-Aminobenzoxazoles under Mild Conditions Journal of Organic Chemistry. ,vol. 76, pp. 7938- 7944 ,(2011) , 10.1021/JO201402A
Jayaraman Dhineshkumar, Manjunath Lamani, Kaliyamoorthy Alagiri, Kandikere Ramaiah Prabhu, A Versatile C-H Functionalization of Tetrahydroisoquinolines Catalyzed by Iodine at Aerobic Conditions Organic Letters. ,vol. 15, pp. 1092- 1095 ,(2013) , 10.1021/OL4001153
Jayaraman Dhineshkumar, Kandikere Ramaiah Prabhu, Cross-hetero-dehydrogenative coupling reaction of phosphites: a catalytic metal-free phosphorylation of amines and alcohols. Organic Letters. ,vol. 15, pp. 6062- 6065 ,(2013) , 10.1021/OL402956B
Chan Sik Cho, Wen Xiu Ren, A recyclable copper catalysis in quinoxaline synthesis from α-hydroxyketones and o-phenylenediamines Journal of Organometallic Chemistry. ,vol. 694, pp. 3215- 3217 ,(2009) , 10.1016/J.JORGANCHEM.2009.06.002
Mitsuru Shindo, Yutaka Yoshimura, Maiko Hayashi, Hiroe Soejima, Takashi Yoshikawa, Kenji Matsumoto, Kozo Shishido, Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates. Organic Letters. ,vol. 9, pp. 1963- 1966 ,(2007) , 10.1021/OL0705200
Rajarshi Samanta, Kiran Matcha, Andrey P. Antonchick, Metal‐Free Oxidative Carbon‐Heteroatom Bond Formation Through C–H Bond Functionalization European Journal of Organic Chemistry. ,vol. 2013, pp. 5769- 5804 ,(2013) , 10.1002/EJOC.201300286
Lijuan Ma, Xianpei Wang, Wei Yu, Bing Han, TBAI-catalyzed oxidative coupling of aminopyridines with β-keto esters and 1,3-diones—synthesis of imidazo[1,2-a]pyridines Chemical Communications. ,vol. 47, pp. 11333- 11335 ,(2011) , 10.1039/C1CC13568F