超原子価ヨウ素(III)を用いる環境調和型酸化反応の開発
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概要
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We have synthesized a novel, nonpolymer-supported recyclable hypervalent iodine (III) reagent, 1,3,5,7-tetrakis [4-(diacetoxyiodo) phenyl] adamantane 3a and its derivatives 3b, c and utilized them in environmentally benign oxidations. The new reagents 3a-c mediate a wide range of oxidative transformations with efficiencies similar to those of conventional reagents, phenyliodine (III) diacetate (PIDA) , pheyliodine (III) bis (trifluoroacetate) (PIFA) , and (hydroxyl (tosyloxy) iodo). benzene (HTIB) , and have higher reactivity compared with polymer-supported recyclable reagents such as poly(diacetoxyiodo) styrene (PDAIS) and poly {bis (trifluoroacetoxy) iodo} styrene (PBTIS). In all cases, tetraiodide 4 was recovered nearly quantitatively in a pure form after simple workup, i.e., filtration. Reoxidation of 4 to 3a with m-chloroperbenzoic acid also proceeded quantitatively, without loss of oxidative activity. Recyclable 3a-c are used in various organic solvents as well as water, and thus mild and clean oxidation of alcohols in water has been achieved using 3a. A facile synthesis of aldehydes from primary alcohols has also been demonstrated using a dual recycling strategy, with 3a and recyclable 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO).
- 2006-09-01