2001
DOI: 10.1016/s0040-4020(00)00941-8
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Efficient oxidative biaryl coupling reaction of phenol ether derivatives using hypervalent iodine(III) reagents

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Cited by 187 publications
(71 citation statements)
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“…A range of arenes worked comparably well under our reaction conditions to give the corresponding biaryls in moderate to good yields (Table 5). Even difficult substrates such as 4-nitroanisole, which was reported to be unreactive in Lewis acid mediated oxidative coupling [35], produced the corresponding biaryl in moderate yield (Table 5, entry 12). Highly electron deficient substrates like 1,3-dicholorobenzene also reacted at elevated temperature (Table 5, entry 16).…”
Section: Introductionmentioning
confidence: 99%
“…A range of arenes worked comparably well under our reaction conditions to give the corresponding biaryls in moderate to good yields (Table 5). Even difficult substrates such as 4-nitroanisole, which was reported to be unreactive in Lewis acid mediated oxidative coupling [35], produced the corresponding biaryl in moderate yield (Table 5, entry 12). Highly electron deficient substrates like 1,3-dicholorobenzene also reacted at elevated temperature (Table 5, entry 16).…”
Section: Introductionmentioning
confidence: 99%
“…[41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] Therefore, various types of recyclable hypervalent iodine reagents have been reported. First, the polymer-supported hypervalent iodine reagents, such as poly(diacetoxyiodo) styrene (PDAIS) and poly[bis(trifluoroacetoxyiodo)] styrene (PBTIS), incorporating phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA) in their polymer backbones were developed.…”
Section: Resultsmentioning
confidence: 99%
“…First, the polymer-supported hypervalent iodine reagents, such as poly(diacetoxyiodo) styrene (PDAIS) and poly[bis(trifluoroacetoxyiodo)] styrene (PBTIS), incorporating phenyliodine(III) diacetate (PIDA) and phenyliodine(III) bis(trifluoroacetate) (PIFA) in their polymer backbones were developed. [41][42][43][44][45][46][47][48] Inspired by this study, other chemists have also reported new recyclable hypervalent iodine compounds having fluorous tags [49][50][51][52] and ionic supports. [53][54][55] We have previously developed a structurally new recyclable hypervalent iodine reagent 1a, namely, 1,3,5,7-tetrakis[4-(diacetoxyiodo) phenyl] adamantane ( Fig.…”
Section: Resultsmentioning
confidence: 99%
“…The hypervalent iodine(III) reagent, PIFA, induced biaryl coupling reaction involving aromatic cation-radical intermediates was originally developed by our group 89,94,95,97) and applied to the synthesis of some useful heterocycles by Moreno et al 109) The commonly used conditions for biaryl coupling reactions using PIFA are as follows: (i) in poorly nucleophilic solvents such as TFE or HFIP; and (ii) in the presence of BF 3 ·Et 2 O (2 eq) in CH 2 Cl 2 .…”
Section: Oxidative Non-phenolic Coupling Reaction Leading To Biarylsmentioning
confidence: 99%