Art

J-GLOBAL ID：201302244691356036   Reference number：13A0817876

Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis

電気化学的に発生した超原子価ヨウ素酸化剤の天然物合成への応用

Author (3)： KAJIYAMA Daichi (Keio Univ., Yokohama, JPN) ,  SAITOH Tsuyoshi (Keio Univ., Yokohama, JPN) ,  NISHIYAMA Shigeru (Keio Univ., Yokohama, JPN)
Material： 電気化学および工業物理化学  (Electrochemistry)
Volume： 81  Issue： 5  Page： 319-324  Publication year： May. 05, 2013 
JST Material Number： G0072A  ISSN： 1344-3542  CODEN： EECTFA  Document type： Article
Article type： 解説  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *electrochemical reaction ,  *iodine ,  *oxidizing agent ,  *chemical synthesis ,  toxicity ,  anodic oxidation ,  nitrogen heterocyclic compound ,  phenolic compound ,  phenol ether ,  polynuclear aromatic compound ,  aromatic iodine compound ,  *hypervalent iodine ,  low toxicity ,  *natural product synthesis

JST classification (3)： Oxidation,reduction  (CF02060T) ,  Electrochemical reaction  (CB07050F) ,  Aromatic monocyclic halogen compounds  (CF05030H)

Substance index (16)： N-1-β-D-Ribofuranosyldamirone C ,  Alline ,  1-Methoxy-1-azaspiro[4.5]deca-7,9-diene-2,6-dione ,  5-Bromo-8-(3-methyl-2-butenyl)-1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-3a-ol ,  CPC-1 ,  N-1-β-D-Ribofuranosylmakaluvamine I ,  Carbazomycin B ,  Glycozoline ,  Siamenol ,  Damirone A ,  Damirone B ,  Damirone C ,  Phenylbis(trifluoromethoxy) iodine(III) ,  Makaluvamine D ,  Makaluvamine I ,  Iodobenzene

Reference (28)：

• 1) L. F. Silva, Jr. and B. Olofsson, Nat. Prod. Rep., 28, 1722 (2011).
• 2) Y. Amano and S. Nishiyama, Tetrahedron Lett., 47, 6505 (2006). General procedure of oxidation with PIFE. A solution of iodobenzene (0.75 mmol, 3 eq. mol) in TFE (25 mL) containing LiClO₄ was electrolyzed (CCE at 0.3 mA/cm², 2.5 F/mol, a glassy carbon beaker as an anode, a platinum wire as a cathode). After electrolysis, the substrate (0.25 mmol) was added: the mixture was stirred at appropriate temperature. After the reaction was completed, the mixture was diluted with H₂O, and extracted with EtOAc. The organic layer was dried and evaporated. The residue was chromatographed on a silica gel column or preparative TLC to give the product.
• 3) Y. Kikugawa and M. Kawase, Chem. Lett., 19, 581 (1990).
• 4) I. Tellitu and E. Dominguez, Synlett, 23, 2165 (2012).
• 5) Y. Amano, K. Inoue, and S. Nishiyama, Synlett, 19, 134 (2008).

Terms in the title (5)： 電気化学 ,  超原子価ヨウ素 ,  酸化剤 ,  天然物合成 ,  応用