Reactions of dichlorine heptoxide and of hypohalites with alkyl iodides

Baum, Kurt; Beard, Charles D.

doi:10.1021/jo00905a027

Cited by 8 publications

(2 citation statements)

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“…While a hypoiodite seems to be the active species, solvolysis of the hypervalent species in ethanol must be envisaged as a plausible initial step. 19 This would eventually lead to ethoxyhypoiodite 15a, 20,21 as the actual active iodination reagent (Scheme 3A). Only ionic intermediates should be considered from this point, since, as demonstrated, adding BHT does not affect the outcome.…”

Section: Scheme 1 Iodine(iii)-mediated Halogenation Of Enamidesmentioning

confidence: 99%

PIFA-mediated ethoxyiodination of enamides with potassium iodide

et al. 2016

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The regioselective ethoxyiodination of enamides was developed using PIFA in combination with potassium iodide in ethanol. The reaction proceeds regioselectively with excellent yields and diastereoselectivities, providing valuable synthons for further functionalisations. Control experiments were conducted, indicating that the transformation occurs through an ionic manifold involving an in situ generated hypoiodite species.

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Section: Scheme 1 Iodine(iii)-mediated Halogenation Of Enamidesmentioning

confidence: 99%

PIFA-mediated ethoxyiodination of enamides with potassium iodide

et al. 2016

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“…Alkyl iodides can be oxidized to their iodine oxidation state of + +III by anumber of oxidizing agentsintroducingi mportant synthetic flexibility. [10] Following the pioneering work by Thiele, [3] as eries of different oxidantss uch as molecularh alogensB r 2 ,C l 2 and F 2 , [11] xenon difluoride, [12] perchlorates, [13] dichloroh eptoxide, [14] and preformed polyvalent iodine reagents [15] have all found successfula pplication in the chemoselectiveo xidation of defined alkyliodine(I)c ompounds to their corresponding high-oxida- tion-state alkyliodine(III) derivatives. The mentioned oxidants usually generate trisubstituted iodine(III) derivatives incorporating two new substituents at the iodine center.…”

Section: General Transformations:applications In Synthesismentioning

confidence: 99%

Alkyliodines in High Oxidation State: Enhanced Synthetic Possibilities and Accelerated Catalyst Turn‐Over

Bosnidou

Muñiz

2019

Chemistry A European J

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In contrast to aryliodine(III) compounds, which have matured into a particularly attractive class of oxidants in modern synthesis, the synthetic potential of related alkyliodine(III) derivatives has remained widely underestimated. This is surprising since several unique synthetic possibilities arise directly from the low stability of their central carbon–iodine bond. In this respect, these high‐oxidation‐state iodine compounds resemble environmentally benign variants of the prominent metal counterparts such as those derived from palladium, nickel and copper. This Concept article summarizes the general reactivity trends in alkyliodine(III) chemistry and discusses selected examples of their strategic use as highly reactive, transient species in organic synthesis and homogeneous catalysis.

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