Oxidation of phenols to quinones by bis(trifluoroacetoxy)iodobenzene.

Barret, Roland; Daudon, M.

doi:10.1016/s0040-4039(00)97755-4

Cited by 99 publications

(44 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Both pentavalent and trivalent iodines react with phenols, but oxidized products were different in some cases. [49][50][51][52] For example, reaction of p-methoxyphenol with IBX provided 4-methoxy-1,2-benzoquinone, 53) in contrast to the reaction with PIFA giving p-quinone. 37) Although it remains unclear whether iodine(V) or iodine(III) species was formed during the reaction, 54) a possible catalytic cycle for this oxidation is shown in Chart 2.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone: Oxidation of p-Alkoxyphenols to p-Benzoquinones

Yakura

Tian

Yamauchi

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Hypervalent iodine compounds, trivalent iodine compounds such as phenyliodine(III) diacetate (PIDA) and phenyliodine(III) trifluoroacetate (PIFA) and pentavalent iodine reagents such as Dess-Martin periodinane (DMP) and o-iodoxybenzoic acid (IBX), have been used extensively in recent organic synthesis because of their low toxicity, ready availability and easy handling. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] However, these reagents are highly expensive. And stoichiometric amounts of iodine reagents are required to produce equimolar amounts of organic iodine waste. Moreover, pentavalent iodine reagents are potentially explosive. To overcome these disadvantages, catalytic hypervalent iodine oxidations [16][17][18] using mchloroperbenzoic acid (m-CPBA), [19][20][21][22][23][24][25][26][27] Oxone ® (2KHSO 5 · KHSO 4 · K 2 SO 4 ), 28,29) and H 2 O 2 30) as a co-oxidant have been reported recently.Development of efficient methods for synthesis of pquinone and p-quinone derivatives is an important subject in synthetic organic chemistry because they are structural components of numerous natural products and useful synthetic intermediates. [31][32][33][34][35][36] A convenient procedure for p-quinones was hypervalent iodine oxidation of p-alkoxyphenols using PIFA.37) Reactions of p-alkoxyphenols with an equimolar amount of PIFA in a 2 : 1 mixture of acetonitrile and water at room temperature gave the corresponding p-quinones in excellent yield.As part of our study for development of practical and environmentally benign oxidation, we report a mild, efficient and practical procedure for catalytic hypervalent iodine oxidation of p-alkoxyphenols to p-quinones using a catalytic amount of 4-iodophenoxyacetic acid (1a) and Oxone ® as a co-oxidant 38) in 2,2,2-trifluoroethanol-water. Results and DiscussionWe chose Oxone ® as an environmentally safe co-oxidant for a catalytic hypervalent iodine oxidation of p-alkoxyphenols because Oxone ® is an inorganic and water-soluble oxidant with a low order of toxicity, moreover, it is commercially available and inexpensive. 39) Oxone ® has been already used as a co-oxidant under heating conditions in the catalytic IBX oxidation by Vinod 28) and Giannis 29) groups, independently. Because alkoxyphenols have high reactivity under oxidation conditions, we first investigated the oxidative ability of Oxone ® itself. 40) A mixture of 2-pivaloyloxymethyl-4-methoxyphenol (2a) and an equimolar amount of Oxone ® in acetonitrile-water (2 : 1) at room temperature gave the corresponding p-benzoquinone (3a), but the reaction was sluggish and the yield of 3a was only 13% along with 78% of recovered starting 2a after 24 h. Next, we examined reactions of 2a in the presence of several iodoarenes as a catalyst (Chart 1). Table 1 presents the results. According to the procedure reported by Vinod, 28) a mixture of 2a, 0.2 equivalents (eq) of 2-iodobenzoic acid, and 1 eq of Oxone ® in acetonitrile-water was heated at 70°C for 19 h to give a complicated mixture (entry 2). However, a similar reactio...

show abstract

Section: Resultsmentioning

confidence: 99%

Catalytic Hypervalent Iodine Oxidation Using 4-Iodophenoxyacetic Acid and Oxone: Oxidation of p-Alkoxyphenols to p-Benzoquinones

Yakura

Tian

Yamauchi

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Compounds 103 and 105 have been converted to corresponding quinones 104 and 106 by oxidation with bis(trifluoroacetoxy) iodobenzene (BTIB). [130][131][132][133][134] The nitric acid oxidation of phenols into the corresponding quinones has been known for a century. Nakao et al 135 used such a protocol in the synthesis of antileukemic agents.…”

Section: Synthesis Of 14-benzoquinones From Phenolsmentioning

confidence: 99%

“…In a two step procedure, Shi et al 162 first demethylated dimethoxy compounds (131) using BBr 3 to yield hydroquinones (132) and then carried out oxidation with Cl 2 /AcOH-H 2 O resulting in the formation of chlorinated quinones (133) (Scheme 26).…”

Section: Synthesis Of Benzoquinones From Dimethoxybenzenesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

170

View full text Add to dashboard Cite

As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

show abstract

“…A subsequent reduction of the nitro group 12 provided aminobenzoxazoles, such as 13, which were oxidized with either FremyÕs salt [potassium nitrosodisulfonate, (KO 3 S) 2 NO] 13 or BTI [bis(trifluoroacetoxy)iodobenzene] 14 to the corresponding quinone 14. Addition of N,N-dimethylethylenediamine to phenylbenzoxalonedione 14 gave a mixture of regioisomers 3b,b 0 and 3c,c 0 .…”

Section: No]mentioning

confidence: 99%