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Dioxoiodane Compounds as Versatile Sources for Iodine(I)
Chemistry
Kilian Muñiz,*[a,b] Belén García,[a] Claudio Martínez[a] and Alessandro Piccinelli[a]
Abstract: The general synthesis, isolation and characterization of
electrophilic iodine reagents of the general formula R4N[I(O2CAr)2] is
reported. These compounds are air- and moisture-stable iodine(I)
reagents, which were characterized including X-ray analysis. They
represent conceptually new iodine(I) reagents with anions as
stabilizers. These compounds display the expected performance as
electrophilic reagents upon interaction with electron-rich substrates.
The performance of these compounds in a total of 47 different
reactions of vicinal iodooxygenation of alkenes is studied and some
key features on the reagents are revealed.

Alternatively, electrochemical oxidation can provide an elegant
approach to generate iodine cations in solution, providing that the
solvent exercises as stabilizing ligand. Yoshida has pursued
this approach and has demonstrated that dimethylsulfoxide as
solvent promotes the formation of solvated iodonium derivatives,
which promote vicinal difunctionalization of alkenes, allenes and
butadienes.[11]

Introduction
Oxidative functionalization of hydrocarbons with iodine reagents
has recently attracted a significant amount of attention.[1,2] In
general, this iodine-based methodology benefits from the
absence of any transition metals and meets with the requirements
of benign synthesis that have been proposed as a key aspect for
modern transformations. Defined electrophilic iodine catalysis has
been at the centre of recent development.[3,4] Molecular iodine
itself is a polarizable molecule that has found wide application as
a pro-electrophile.[1,2] Common electrophilic iodinating reagents
mostly rely on preformed N-iodo amides such as Niodosuccinimide (NIS).[5] Apart from such N-iodinated reagents,
stabilized halonium reagents have been at the centre of attention
and have found widespread application in organic synthesis.
These reagents represent an umpolung version of the common
nucleophilic iodine and thus allow for a series of iodinating
reactions that are not accessible by classic means.[6]
A major accomplishment in the area rests with the recognition by
Barluenga that stabilization of the iodonium atom can be
accomplished by pyridine moieties.[7-10] The resulting complex
was prepared in form of the corresponding tetrafluoroborate salt
and represents a stable reagent for convenient iodination of
organic molecules. Among the prominent reaction pathways that
were uncovered for this reagent, iodooxygenation of alkenes was
among the first that were investigated.[7]

[a]

[b]

Prof. Dr. K. Muñiz, B. García, Dr. C. Martínez, A. Pccinelli
Institute of Chemical Research of Catalonia (ICIQ),
The Barcelona Institute of Science and Technology,
Av. Països Catalans 16, 43007 Tarragona, Spain
E-mail: kmuniz@iciq.es
Prof. Dr. K. Muñiz
ICREA,
Pg. Lluís Companys 23, 08010 Barcelona, Spain
Supporting information for this article is given via a link at the end of
the document.

Figure 1. Stable iodine(I) compounds.

These compounds are characterized by the stabilization of
cationic iodine cores with neutral ligands. An alternative would be
the linear coordination of two anionic ligands to provide an overall
monoanionic complex. We have recently reported the synthesis
of such a new stable iodine(I) compound, which represents the
tetrabutylammonium derivative of the catalyst resting state in an
iodine catalyzed Hofmann-Löffler reaction.[12] Obviously, in this
type of C-H amination reaction the specific reactivity of the
electrophilic iodine(I) reagent gives rise to an N-iodination, which
is the origin of the required radical-based reactivity.
We speculated that in addition the isolated iodine(I) reagent
should be able to display typical reactivity of electrophilic halide
derivatives. We here provide the full account on the accessibility
of electrophilic iodine reagents of the general formula
R4N[I(O2CAr)2] and their reactivity towards alkenes within a vicinal
iodooxygenation reaction.[13,14,15]

Results and Discussion
Reagent synthesis, structure, solution behavior. The
synthesis of dioxoiodanes is general for a number of different
benzoates as ligands. It follows the general synthetic outline from
Scheme 1 and is based on an effective comproportionation
reaction that originates from the reaction between an ammonium

iodide 1 and a hypervalent iodine(III) reagent 2.[16] Compounds 3
are isolated as white to yellow solids that display reasonable
stability against air and moisture.

Scheme 1. Synthesis of iodine(I) reagents of the general formula
R4N[I(O2CAr)2].

Four of the new compounds were submitted to further analysis by
X-ray diffraction of single crystals. The corresponding structures
of compounds 3f, 3g, 3i and 3k are depicted in Figure 2[17] and
compliment the one of compound 3e reported earlier.[12] The key
features of these compounds are (i) the expected linear
coordination mode of the anionic carboxylates at the central
iodine atom and (ii) the rather short iodine-oxygen bond distances
in the range of 2.16 to 2.20 Å. This demonstrates a shorter
bonding and thus stronger interaction for the anionic ligands than
in comparable pyridine (2.255-2.261 Å)[18,19,20] and dmso adducts
(2.27 Å).[11]

Figure 2. Solid state structures of compounds 3f, 3g, 3i and 3k (ORTEP plots
at 50% probability). Selected bond lengths (Å) and angles (º). 3f: I1A-O1A#1
2.1835(18), I1A-O1A 2.1836(18), O1A-I1A-O1A#1 180. 3g: I1-O1 2.193(5), O1I1-O1’ 179.8(2). 3i: I1-O1 2.177(8), I1-O4 2.162(8), O4-I1-O1 168.7(7). 3k: I1O1 2.1962(10), I1-O3 2.2021(11), O1-I1-O3 176.62(4).

Iodine reagents 3 display a remarkable stability in solution. A
control experiment with a solution of the two fluorinated
compounds 3b and 3g displayed no anion scrambling according
to monitoring by 19F NMR confirming that the two anionic iodine
units remained stable under neutral conditions (Scheme 2).[21]

reactions of 3n and 3p and activation with benzoic acid, which
provided 4:1-product mixtures of 5n and 5a and 59 and 5a,
respectively, regardless of the electronic substitution, since the
donor substituent in 3n leads to an identical outcome as in case
of the acceptor substituent in 3p.

Scheme 2. Experiment on solution stability of iodine(I) compounds 3.

Reagent performance in alkene oxidation. The behavior of
compounds 3 towards styrenes was investigated. Based on the
known propensity of iodine(I) reagents to induce iodooxygenation
reactions, this particular reaction was employed for an exploration
in the present case (Scheme 3). As observed for the complete set
of 16 examples, all reagents 3 provided the corresponding 1,2difunctionalized products in 60-93% isolated yield. The best yield
was obtained with the 3-chlorobenzoate derivative 3e. It is
noteworthy that products 5 display pronounced stability regarding
the carbon-iodine bond. For example, no undesired derivatization
as could for example result from Woodward pathway[22] was
observed in any of the cases.

Scheme 3. Iodooxygenation of styrene 4a with the set of reagents 3.

For the reactions from Scheme 3, the reagents 3 were activated
by addition of an equimolar amount of free carboxylic acid, which
greatly accelerates the reaction. While reagents 3 are reactive by
themselves, the corresponding reactions are comparably slow.
The observed acceleration by free acid has been invoked to be
the result of a transformation of the ammonium salts 3 into the
free acids, which readily give rise to the active reagent I-O2CAr
(Scheme 4). It is important to note that activation with a different
acid is possible, but leads to formation of product mixtures due to
anion scrambling. This context was clarified for representative

Scheme 4. Experiment on the role of acid activation in the iodooxygenation of
styrene 4a.

Despite the uniform high yields observed in the vicinal
difunctionalization from Scheme 3, it remained of interest to study
potential substitution effects on the initial rate of iodooxygenation.
As represented in Figure 3, such electronic influences are indeed
present in oxidation of styrene 4a with different iodine(I) reagents.
To avoid any potential steric influence on the reaction rate, the 4substituted benzoic acid derivatives 3n-q were compared to
reagent 3a with benzoic acids as ligands to iodine. As can be
observed from the relative rates, electron-attracting substitution
enhances the initial rate of the reaction. This is in agreement with
the qualitative expectation that less stabilized carboxylate ligands
in 3 will lead to a more rapid liberation of the active reagent IO2CAr, which in addition will be of more pronounced electrophilic
character.
The corresponding Hammett plot supports this analysis. Based on
the initial rates of the individual reactions, a linear relationship is
obtained between the logarithm of the rate fractions versus the
Hammett s values (Figure 3, bottom). The graphical correlation
yields a corresponding r value of 0.78, which is indicative of a
build up of electrophilicity in the slow step of the reaction as
discussed before.

Scheme 5. Iodooxygenation of styrenes 4a-r with reagent 3e.

Figure 3. Effect of the 4-substitution on the initial rate of the iodooxygenation of
styrene 4a with different iodine reagents (top) and Hammett correlation
(bottom).

Since in the investigation from Scheme 3 the highest yield in
styrene iodooxygenation was obtained with compound 3e, further
studies regarding the general scope of iodooxygenation reactions
were conducted using this reagent. As demonstrated in Scheme
5 for 17 examples, the corresponding vicinal difunctionalization
reactions proceed for a series of different substitution patterns at
the arene core, which includes individual 2-, 3- and 4-substitution
as in products 6b-o and in higher-substituted derivatives 6p-r.
The same substrate tolerance is observed for a-substituted
styrenes 7a-g, which give rise to the corresponding products 8ag in 55-98% isolated yield. As in the case of the previous
examples, all reactions proceed with complete regio- and
chemoselectivity in favor of the iodine incorporation at the terminal
position. This observation is consistent with the general
expectation of a mechanism that involves an iodonium
intermediate resulting from alkene addition to the electrophilic
iodine center in reagents 3 followed by nucleophilic benzoate
opening at the benzylic position.

Scheme 6. Iodooxygenation of a-substituted styrenes 7a-g with reagent 3e.

It is noteworthy that these vicinal iodooxygenation reactions
proceed with stereospecificity regarding the geometry of internal
double bonds. This was demonstrated for (Z)- and (E)-b-methyl
styrenes 9a and b. While the latter one provided a single
stereoisomeric product 10b, the former one yielded the opposite

isomer 10a, together with a minor amount of isomerization
(Scheme 7). This result compares well with the outcome for the
related cationic I(dmso)2 reagent.[11a] Cyclic alkenes such as 9c
and 9d also give the corresponding regioselective products 10c
and 10d with the expected stereoselectivity.

3e led to the formation of a single regioisomeric product 12a,
which is the thermodynamically preferred product due to
maintenance of the styrene conjugation. 2-Aminostyrene also
constitutes an interesting substrate. While its Cbz-protected
derivative 4t behaves as the styrene derivatives from Scheme 5
and thus undergoes clean iodooxygenation to 5s, the
corresponding tosylamide 4s promotes an aminooxygenation to
the 3-oxygenated indoline 12b. Interestingly, this product proofed
to be stable against indole formation[24] via elimination. A related
cyclization was attempted with 11c as precursor to
iodolactonization.[25] However, the allyl ester 12c[26] was formed
as the only product, which is believed to result from an acid
exchange between 3e and 11c to provide the iodine(I) derivative
of 11c, which undergoes iodine-promoted decarboxylation[27]
followed by oxygenation to the allylic product.

a

Scheme 7. Iodooxygenation of internal alkenes 9a-d with reagent 3e. General
conditions: 3-chlorobenzoic acid (1.2 equiv), 3e (1.2 equiv), CH2Cl2, 25 ºC, 12
h. Ar = 3-Cl-C6H4.

a

Scheme 8. Further examples on oxidation of alkenes 4s,t,11a,b with reagent
a
3e. General conditions: 3-chlorobenzoic acid (1.2 equiv), 3e (1.2 equiv),
CH2Cl2, 25 ºC, 12 h. Ar = 3-Cl-C6H4.

Further reactivity was explored for additional substrates such as
the 1,3-butadiene 11a (Scheme 8). As expected from a related
diamination with hypervalent iodine reagents,[23] the reaction with

Scheme 9. Iodooxygenation upon activation of reagent 3c with amides.
19
b
Conversion by F NMR with fluorobenzene as internal standard. Isolated yield
after purification.

Finally, a recent report by Hayashi on the possible activation of Niodosuccinimide with amine groups (Scheme 9)[28] prompted the
investigation on related reactivity in the present system. While
allylamine turned out to be incompatible with iodine(I) reagent 3c,
related acetamides promoted the iodooxygenation of 4-

fluorostyrene 4g to the corresponding product 6t in a way that is
comparable to activation with 2-chlorobenzoic acid. Although due
to instability in solution, no structural data has become available
yet, an activation of the iodine(I) by acetamide similar to the case
of Hayashi is proposed to be involved in this case.
This outcome demonstrates that there are further possible
activation modes for compounds 3 in metal-free oxidation
reactions. Exploration of such pathways as well as the
combination of reagents 3 as oxidants in transition metal
mediated and catalyzed transformations are currently under
progress.

ICIQ Program (fellowship to C. M.). The authors are grateful to E.
Escudero-Adán for support with the X-ray analyses.
Keywords: Alkenes • Iodine • Difunctionalization • Synthetic
Methods • Oxidation
[1]
[2]

[3]

Conclusions
[4]

We have presented the general synthesis of isolable, air-stable
electrophilic iodine(I) reagents, which are stabilized by
coordination of two carboxylate units. Their structures and
solution behavior have been discussed in detail. These
compounds add to an existing number of stable iodine(I)
precursors as sources for electrophilic reagents. Their versatile
applicability to organic synthesis has been demonstrated by a
number of chemo- and regioselective iodooxygenation reactions
of styrenes. Their synthetic potential remains yet to be fully
explored, and there are reasons to expect that the new
compounds will be able to make future impact.

[5]
[6]

[7]
[8]
[9]
[10]

Experimental Section
General procedure for the synthesis of iodine derivatives 3: The
synthesis was adapted from a recently published procedure.[12] A Schlenk
tube equipped with a stirrer bar was charged with the corresponding
iodine(III) compound (1.0 equiv), the ammonium iodide (2.17 mmol, 1.0
equiv), evacuated and backfilled with argon. At this point, 4 mL of CDCl3
were added. The solution was stirred at 25 ºC for 12 h. Et2O was then
added to induce precipitation of a solid, which was filtered and washed
with Et2O. The compound was dried under reduced pressure to obtain the
pure title compound.
General procedure for the difunctionalization reaction of alkenes. A
Schlenk tube equipped with a stirrer bar was charged with 3-chlorobenzoic
acid (1.2 equiv), tetrabutylammonium bis((3-chlorobenzoyl)oxy)iodate(I)
(1.2 equiv) and (3 mL) of dry dichloromethane. The corresponding styrene
(0.2 mmol, 1 equiv) was added and the reaction was stirred overnight at
30 ºC. Then DCM was added and the solution was washed with a
saturated aqueous solution of Na2S2O3. The organic phase was dried over
Na2SO4, filtered and the solvents were removed under reduced pressure.
The crude product was purified by flash column chromatography
(hexane/EtOAc, 9:1) to provide the corresponding iodooxygenated
products.

Acknowledgements
Financial support for this project was provided from the Spanish
Ministry for Economy and Competitiveness and FEDER
(CTQ2014-56474R grant to K. M., and Severo Ochoa Excellence
Accreditation 2014-2018 to ICIQ, SEV-2013-0319) and Cellex-

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[13]

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FULL PAPER
Kilian Muñiz,* Belén García, Claudio
Martínez, Alessandro Piccinelli.
Page No. – Page No.
Dioxoiodane Compounds as Versatile
Sources for Iodine(I) Chemistry
Stable and readily applicable for oxidation. A family of new iodine(I) derivatives
is presented, which enables a number of alkene difunctionalization reactions under
convenient conditions.