Chiral Hypervalent Iodine Reagents: Synthesis and Reactivity

Parra, Alejandro; Reboredo, Silvia

doi:10.1002/chem.201302220

Cited by 173 publications

(39 citation statements)

References 152 publications

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“…Various classes of chiral aryl iodides were examined as potential catalysts, including chiral resorcinol derivatives such as 2a–2d , 7,15 which have found application previously in a variety of enantioselective alkene oxidation reactions. 16 In the presence of catalysts 2a–d , m CPBA as oxidant, and pyr•9HF as the fluorine source and acid promoter, 1a was observed to undergo cyclization to fluoroisochromanone 3 as a single observable diastereomer (Table 1). 17 The syn relative configuration was determined via X-ray crystallographic analysis, consistent with the reaction pathway outlined in Scheme 2.…”

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confidence: 99%

Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

2016

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The enantioselective synthesis of 4-fluoroisochromanones via chiral aryl iodide-catalyzed fluorolactonization is reported. This methodology uses HF•pyridine as a nucleophilic fluoride source with a peracid stoichiometric oxidant, and provides access to lactones containing fluorine-bearing stereogenic centers in high enantio- and diastereoselectivity. The regioselectivity observed in these lactonization reactions is complementary to that obtained with established asymmetric electrophilic fluorination protocols.

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confidence: 99%

Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

2016

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“…Large array of reactions such as coupling of phenols, oxidation of sulfides, α ‐functionalization of ketones and alkene, oxidation of alcohol, biaryl coupling, CH functionalization, etc., make use of hypercoordinate iodine reagents . Development of hypercoordinate iodine chemistry and its synthetic applications have been extensively documented and even reviewed in the literature.…”

Section: Introductionmentioning

confidence: 99%

Hypercoordinate iodine(III) promoted reactions and catalysis: an update on current mechanistic understanding

Sreenithya

Surya

Sunoj

2017

WIREs Comput Mol Sci

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Mild and environment friendly hypercoordinate iodine compounds exhibit promising reactivities resembling that of transition metal catalysts. Hypercoordinate iodine reagents or catalysts are increasingly been employed in contemporary organic synthesis. However, mechanistic insights on such reactions continue to remain rather limited. Recent advances in the mechanistic understanding on a selected set of reactions involving hypercoordinate iodine form the main theme of this review. An overview of bonding, reactivity, and mechanistic insights on iodine(III) reactions such as α-functionalization of carbonyl compounds, alkynylation, amination, C H functionalization, phenol dearomatization, and trifluoromethylation have been described. In keeping with the current practices in mechanistic studies, we have maintained an interdisciplinary flavor in this compilation by providing a balanced view of computational and experimental understanding on the burgeoning domain of hypercoordinate iodine mediated reactions and catalysis. FIGURE 1 | Molecular orbital (MO) diagram for three-center-fourelectron (3c-4e) bond in hypercoordinate iodine compound RIL 2 . SCHEME 1 (a) General representation of α-tosyloxylation ketone catalyzed by Koser's reagent. (b) General mechanism for the α-tosyloxylation ketone. (c) Commonly employed iodoarenes in α-tosyloxylation. Overview wires.wiley.com/compmolsci SCHEME 2 (a) Effect of different substituents on the catalytic activity of iodoaryl in α-tosyloxylation. (b) Effect of different substituents on dihedral angle θ(C1-C2-I3-O4). (c) Formation of iodono intermediate 4 and the related ΔG rxn . WIREs Computational Molecular Science Hypercoordinate iodine(III) promoted reactions and catalysis Volume 7,

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“…The intense interest is mainly due to the remarkable oxidizing properties of hypervalent iodine reagents and their attractive features such as easy to handle, low toxicity, availability of supply, and environmental benignity. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Two of their most important synthetic applications are in the constructions of heterocyclic skeletons and functionalization of heterocycles, such as three-to seven-membered rings and spiro compounds, under metal-free reaction conditions. Some representative transformations have been shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent iodine reagents for heterocycle synthesis and functionalization

Sun¹,

Zhang‐Negrerie²,

Du³

et al. 2016

ROC

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Hypervalent iodine reagents have been vastly applied in many significant oxidative reactions. This surging interest in iodine reagents is mainly due to the very useful oxidizing properties, combined with their benign environmental character and commercial availability. In this review, we focus on the representative transformations that used the common hypervalent iodine reagents as oxidants in heterocycle synthesis and functionalizations, based on the type of the hypervalent iodine reagents.

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Chiral Hypervalent Iodine Reagents: Synthesis and Reactivity

Cited by 173 publications

References 152 publications

Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source

Hypercoordinate iodine(III) promoted reactions and catalysis: an update on current mechanistic understanding

Hypervalent iodine reagents for heterocycle synthesis and functionalization

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