<i>Para</i>-Selective Cu-Catalyzed C–H Aryloxylation of Electron-Rich Arenes and Heteroarenes

Sokolovs, Igors; Sūna, Edgars

doi:10.1021/acs.joc.5b02728

Cited by 34 publications

(19 citation statements)

References 59 publications

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“…Sokolovs and Suna recently reported a one-pot two-step procedure for the para-selective C-H aryloxylation of electron-rich (hetero)arenes 174. 84 In analogy with their previously described strategy for the indirect amination 57,58 and azidation 78 of this type of substrate, the authors described that in situ generated unsymmetrical diaryliodonium salts 175 reacted with phenols 176 under copper catalysis to afford diaryl ethers 177 in good yields (Scheme 55). The Cu(I) catalyst is responsible for the selective transfer of the electron-rich ligand of the diaryliodonium salt.…”

Section: Scheme 53 Copper-catalyzed Monoarylation Of Vicinal Diols Wimentioning

confidence: 99%

Copper-Catalyzed Arylation with Diaryliodonium Salts

Fañanás‐Mastral

2017

Synthesis

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The unique reactivity of diaryliodonium salts with copper complexes has been applied to a variety of synthetic organic transformations. These hypervalent iodine compounds have been used for diverse copper-catalyzed cross-coupling reactions including C-H functionalizations, enantioselective CC bond formation, cascade reactions and different heteroatom arylation processes. This review provides a summary of recent developments on this topic and discusses both the synthetic utility and mechanisms of these transformations.

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Section: Scheme 53 Copper-catalyzed Monoarylation Of Vicinal Diols Wimentioning

confidence: 99%

Copper-Catalyzed Arylation with Diaryliodonium Salts

Fañanás‐Mastral

2017

Synthesis

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“…The results are however different in case of metal-catalyzed reactions. Suna et al demonstrated that the presence of a Cu(I) catalyst directed the selectivity of the arylation to the more electron-rich heteroarene moiety during the reaction between heteroaryliodonium salts 35 and phenols (Sokolovs and Suna, 2016) (Figure 2A, Equation c). This Cu(I)-catalyzed synthesis of diaryl ethers using diaryliodonium salts is a complementary strategy to the previously mentioned metal-free arylation of phenols.…”

Section: Heteroaryliodonium Salts As Highly Reactive Pseudo-halidesmentioning

confidence: 99%

Heteroaryliodonium(III) Salts as Highly Reactive Electrophiles

2020

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In recent years, the chemistry of heteroaryliodonium(III) salts has undergone significant developments. Heteroaryliodonium(III) salts have been found to be useful synthetic tools for the transfer of heteroaryl groups under metal-catalyzed and metal-free conditions for the preparation of functionalized heteroarene-containing compounds. Synthetic transformations mediated by these heteroaryliodonium(III) salts are classified into two categories: (1) reactions utilizing the high reactivity of the hypervalent iodine(III) species, and (2) reactions based on unique and new reactivities not observed in other types of conventional diaryliodonium salts. The latter feature is of particular interest and so has been intensively investigated in recent decades. This mini-review therefore aims to summarize the recent synthetic applications of heteroaryliodonium(III) salts as highly reactive electrophiles.

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“…[9] According to our reaction design, a mild Cu-catalyzed intramolecular C—H arylation of alcohols [10] affording dihydrobenzofurans will be accomplished via the intermediacy of non-symmetric diaryliodonium salts, which were to be prepared in situ and processed further without isolation. The choice of the prototypical substrate, 2-(3-methoxyphenyl)-2-cyclohexen-1-ol ( 1 , Table 1) was influenced by its relevance to eventual synthesis targets (galantamine, morphine).…”

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confidence: 99%