A mild carbon-boron bond formation from diaryliodonium salts

Article abstract of DOI:10.1039/c5cc04944j

The direct metal-free borylation of diaryliodonium salts with diboron reagents is now demonstrated to be a feasible process toward formation of aryl boronic esters without any additive or catalysts, and it can be extended to a two-step C-C coupling of both aryl groups of the initial diaryliodonium reagent.

Full text of DOI:10.1039/c5cc04944j

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A mild carbon-boron bond formation from diaryliodonium salts
N. Miralles,a R. M. Romero,b E. Fernández,a* K. Muñizb,c
*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
The direct metal-free borylation of diaryliodonium salts with
diboron reagents is now demonstrated to be a feasible process
toward aryl boronic esters formation without any additive or
catalysts, and it can be extended to a two-step C-C coupling of
both aryl groups of the initial diaryliodonium reagent.
promoter. In principal, the synthetic approach to such a type of
direct C-B bond formation appears unconventional at first sight, as
it involves the combination of two reactants that are of exceedingly
electrophilic nature (Scheme 1, eq. 2).
common arylation employing nucleophilic reaction partners
Due to their ready availability and high stability, diaryliodonium
salts 1 constitute an attractive class of compounds that have been
recognized as particularly versatile aryl transfer reagents.1
Consequently, they have been involved in a series of arylation
reactions, which have been mostly aided by the presence of
transition metal catalysts. While initially C-C bond forming reactions
had been explored to a larger extent, carbonheteroatom bond
forming events based on diaryliodonium salts have been
investigated in greater detail in recent years (Scheme 1, eq. 1).2-10
Among all these accomplishments, carbon-boron bond formation
toward aryl boronic acid derivatives is notably absent.
X
+
Nu
(1)
Ar Nu
+ Ar-I + X
I
Ar
Ar
arylation of boron groups: strategy
R
R
R
R
R
R
Lewis base
LB
X
X
B
B
B
I
I
+
+
Ar
Ar
Ar
Ar
LB
B
umpolung
R
R
electrophilic electrophilic
reactant reactant
electrophilic nucleophilic
reactant reactant
R
(2)
Ar
B
R
Arylboronic acids and esters are key components for modern cross-
coupling reactions and advanced synthetic transformations.11 Their
high versatility has made C-C coupling events based on them one of
the most versatile themes in the field,12 which was recognized by
the Nobel prize for Suzuki in 2010.13 Common approaches to this
type of reagents employ the original Miyaura-type borylation
reaction between aryl halides and bis(pinacolato)diboron (pinB–
Bpin, 2a) in the presence of catalytic amounts of palladium
C-B coupling
product
Scheme 1. Conceptual approaches to carbon-heteroatom bond
formation using diaryliodonium salts
To accomplish the targeted carbon-boron bond formation, we
envisioned that presence of Lewis base could be employed for the
activation of the diboron reactant. Such an interaction should be
favorable as it provides an umpolung of the native electrophilic
boron atom. The resulting nucleophilic character17 at one of the
boron centers then ensures for effective C-B bond formation with
the electrophilic iodine(III) reagent. This approach is reminiscent of
previous alkoxide base mediated reactions developed by some of
us18,19 and others.20.21 A subsequent screening between various
diphenyliodonium salts 1a-d and bis(pinacolato)diboron (2a) was
undertaken and for the acetate derivative 1d confirmed the
correctness of the initial hypothesis (Scheme 2). In agreement with
previous experience,18,19 methanol was identified as the best
solvent.22 For the reaction between acetate derivative 1d and 2a,
the expected product 3a was formed in high yield and isolated in
complexes. The key intermediate [LPd(Ar)(OAc)] undergoes
a
transmetallation process with 2a.14 Other transition metal
complexes have catalyzed the aryl halide borylation15
complementing the C-H activation of arenes by borane reagents.16
We here report the unprecedented direct formation of aryl boronic
esters, in particular aryl pinacolboranes, through an effective
coupling between diaryliodonium salts and bis(pinacolato)diboron
2a under mild conditions and without any requirement for a metal
a.Department Química Física i Inorgánica, University Rovira i Virgili, C/Marcellí
Domingo s/n, 43007 Tarragona (Spain). Mariaelena.fernandez@urv.cat
b.Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007
Tarragona (Spain). kmuniz@ICIQ.ES
c. Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís
Companys 23, 08010 Barcelona, (Spain)
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77%. This successful transformation leads to two important aryl halides with Bpin-Bdan (2e), which required the presence of a
conclusions: First, methanol as solvent may play a crucial role in palladium- XPhos catalyst under basic conditions.24
activating the diboron reagent through a state such as A. Secondly,
the pronounced dependence of the reaction on the counterion of
O
O
AcO
the diphenyliodonium reagent suggests a crucial participation of
this anion as well. This may include a direct interaction between the
B
B
MeOH
50 ºC
X
X
I
+
B
X
X
solvated acetate with the diboron reagent (state B) or
a
3b-e
2b-e
participation of its negative charge throughout the hydrogen-
bonding network of the protic solvent (state C). For the latter
scenario, the activation is reminiscent of the more common
activation with methoxide base. Obviously, the anions from
compounds 1a-c do not display sufficient basicity to induce
activation of the diboron reagent. The importance of the polar
protic solvent is evident from a comparison of a reaction in polar
unprotic THF, which led to a significantly lower yield of 39% of 3a.22
1d
O
O
O
O
B
B
3b
: 41 (37)%
3c: 46 (34)%
O
B
O
HN
B
HN
3d: 63%[a]
3e
: 87 (52)%
O
O
O
O
X
MeOH
50 ºC
Scheme 3. Borylation of diphenyliodonium salts: influence of the
diboron reagent X = O, NH. Reaction conditions: (C6H5)2IOAc (0.2
mmol), diboron reagent (0.3 mmol), 50 ºC, 1.25 mL methanol, 24 h;
yield calculated by GC spectroscopy with mesitylene as internal
standard as an average of two reactions; isolated yields given in
brackets calculated from (C6H5)2IOAc; [a] Isolated yield of the
corresponding alcohol after oxidative work up.22
B
B
O
O
I
+
B
- pinBX
- PhI
3a
1a-d
1a-c (X = Cl, PF6, OTf):
2a
no conversion
91 (77)%
1d
(X = OAc):
O
O
O
O
O
O
MeOH
50 ºC
O
B
H
O
O
O
O
O
[HOMe]n
AcO
OAc
Ar
B
B2pin2
+
B
B
B
H
I
OMe
Ar
Ar
OAc
OMe [HOMe]n
B
B
O
O
4a-18a
4-18
A
B
C
O
O
B
O
O
O
Cl
F3C
Ph
B
Br
F
B
O
Scheme 2. Borylation of diphenyliodonium salts: optimization with
B2pin2. [a] Reaction conditions: (C6H5)2I+X- (0.2 mmol), B2pin2 (0.3
mmol), 50 ºC, 1.25 mL solvent, 24 h; average yield from two
independent runs calculated by GC spectroscopy with mesitylene as
internal standard; the value in parenthesis refers to an isolated
yield based on (C6H5)2IOAc
6a
9a
62 (45)%
4a 67 (41)%
5a 50 (43)%
O
B
O
O
B
O
O
B
O
MeO
PhO
83 (71)%
7a 71 (56)%
8a 96 (76)%
F3C
MeO2C
O
B
O
B
O
B
O
O
O
10a
88 (72)%
11a 85 (65)%
12a 65 (41)%
With the conceptual verification of the C-B bond formation in hand,
the reaction was further extended to various diboron compounds
for aryl-boron coupling (Scheme 3). For example, products 3b and
3c are conveniently generated from treatment between
diphenyliodonium acetate and bis(neopentylglycolato) diboron (2b)
and bis(hexyleneglycolato)diboron (2c), respectively, as in the case
of the parent transformation with bis(pinacolato)diboron (2a). The
same protocol was also applicable for the related
bis(catecholato)diboron (2d) to furnish the coupling product 3d.
Due to the notorious instability of the catecholboryl derivative, the
O2N
O
B
O
O
B
O
O
B
O
15a
63 (51)%
13a 63 (31)%
14a 48 (40)%
O
B
O
O
B
O
O
B
O
17a 58 (51)%
16a
18a
54 (34)%
93 (57)%
boronic ester was transformed into phenol upon oxidative work- Scheme 4. Borylation of diphenyliodonium salts: reaction scope
up.22a Finally, an excellent result was obtained using the mixed with B2pin2. Reaction conditions: Ar2IOAc (0.2 mmol), B2pin2 (0.3
diboron reagent Bpin-Bdan (2e) (dan = 1,8-diaminonaphthalene),23 mmol), 50 ºC, 1.25 mL methanol, 24 h; average yield from two
which underwent selective activation at the more electrophilic Bpin independent runs calculated by GC spectroscopy with mesitylene as
center.19 This promotes the transfer of the Bdan entity to internal standard; values in brackets refer to isolated yields based
selectively generate C-B coupling product 3e in 87% conversion and on Ar2IOAc.
52% isolated yield. There is only one precedence on borylation of
2 | J. Name., 2012, 00, 1-3
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The scope of the reaction has been evaluated for a number of one of the aryl groups, the more pronounced chemoselectivity
symmetric diaryliodonium salts, which includes ortho-, meta and favoring 3a is observed, regardless the electronic nature of the
para-substitution pattern as well as higher substituted aromatic substituents on the neighboring aryl group. Interestingly, the
entities (Scheme 4). As to a general trend, electron releasing groups reaction of 23 with 2e is conducted towards the formation of 3e
on the 4-substituted aryls of Ar2IOAc contribute to a higher and 3a in 9:1-ratio, showing that steric factors are predominant.
percentage of borylated product formation (8a-10a) in comparison Finally, the successful development of the C-B bond forming
with the electron-withdrawing functional groups (products 4a-7a). reaction was extended to an in situ cross coupling reaction. Since
On the contrary, 3-substituted aryl groups in Ar2IOAc bearing the borylation reaction of the diaryliodonium salts 1 generates an
electron-withdrawing substituents favor the borylation with the equimolar amount of free aryl iodides, submission of the crude
activated B2pin2 (products 11a-13a), while the corresponding reaction mixture to Suzuki-Miyaura cross-coupling should result in
diaryliodonoum salt with 3-tolyl groups is transformed into coupling an overall diaryl synthesis. Such a process would make economic
product 14a in moderate yield. As regularly encountered in use of both of the aryl groups of the diaryliodonium precursor.
arylboronates, yields can diminish during the purification step, Transformations of this kind are rare. Within this context,
being comparable to the most recent achievement in Zn catalyzed Beletskaya reported an exhaustive Suzuki-Miyaura coupling
borylation of aryl halides.25
between diaryliodonium salts and sodium tetraphenylborate,26
Interestingly, the highly substituted aryl(pinacolboronate) esters Nachtsheim developed two sequential C-N bond forming events of
15a-18a are quantitatively formed demonstrating that the present cyclic diaryliodonium salts with anilines to yield N-arylated
method provides a great tolerance to formation of sterically carbazoles27 and Greaney recently reported on the use of both aryl
encumbered aryl boronates.
groups of diaryliodonium salts in 1,3- difunctionalization of
indoles.28 Indeed, the anticipated reaction sequence comprising the
C-B bond formation as a transient path to C-C coupling could be
realized. After the borylation reaction, the solvent was changed
from MeOH to toluene followed by addition of the palladium
catalyst Pd(PPh3)4 and carbonate base (Scheme 6). By this, the
mentioned product mixtures from C-B bond formation with
symmetric diaryliodonium salts engage in the desired direct Suzuki-
Miyaura coupling to provide the corresponding diaryl compounds
25-28 as the only C-C coupling products.
B2pin2
(1.5 equiv)
AcO
O
O
O
O
I
+
F3C
B
B
MeOH, 50 ºC
7a
19a
F3C
80%, 7a:19a = 1:1
19
AcO
HN
B
HN
HN
B
HN
Bpin-Bdan
I
+
F3C
MeOH, 50 ºC
7e
19e
F3C
7e 19e
79%,
:
= 63:37
19
AcO
AcO
R
B2pin2
(1.5 equiv)
O
O
O
R
R
2a
1) B2pin2
(1.5 equiv),
+
B
B
R
I
I
MeOH, 50 ºC
O
MeOH, 50 ºC
R
R
R
3a
8a
7a
2) Pd(PPh3)4 (10 mol%),
Cs2CO3 (2 equiv),
toluene, 80 ºC
(R = H),
(R= CF3),
18a
R
R
(R= OMe).
20
22
21
R
(R = H),
(R= OMe).
(R= CF3),
80%, 3a : 18a = 62:38
7a 18a
95%,
:
= 67:33
94%, 8a : 18a = 56:44
AcO
B2pin2
(1.5 equiv)
iPr
iPr
O
B
O
O
I
Cl
Cl
+
B
iPr
MeOH, 50 ºC
O
iPr
iPr
R
iPr
3a
24a
26
25
27
: 72%
: 87%
23
65%, 3a:24a = 85:15
AcO
HN
B
HN
PhO
OPh
Bpin-Bdan
O
I
+
B
MeOH, 50 ºC
O
: 42%
28: 65%
20
3e
3a
80%, 3e:3a = 9:1
Scheme 5. Borylation of non-symmetric diphenyliodonium salts.
Scheme 6. One pot cross coupling from diaryliodonium salts via
B2pin2. Reaction conditions for activation: Ar1Ar2IOAc (0.2 mmol),
With the aim to explore a selective mixed borylation we conducted B2pin2 (0.3 mmol), 50 ºC, 1.25 mL MeOH, 24 h, reaction conditions
two parallel strategies: i) the reactivity of the novel non-symmetric for cross-coupling: Pd(PPh3)4 (10 mol%), Cs2CO3 (2 eq), 80 ºC, 2 mL
diaryliodonium salts 19-23 with B2pin2 and ii) the reactivity of toluene, 16 h. Yields refer to isolated yields based on Ar1Ar2IOAc.
electronically and sterically mixed diaryliodonium salts 19 and 20
with the mixed diboron reagent Bpin-Bdan (2e). Scheme
5
Conclusions
demonstrates that sterically encumbered aryl boronates exert the
higher degree of selective borylation when reacted with both In summary, we have developed a new protocol for the metal-free
symmetrical and mixed diboron compounds. Therefore, the formation of aryl-boron bonds. It employs readily available
diaryliodonium salt 19 reacts with 2a to give 7a and 19a in a 1:1- diaryliodonium acetates and commercially available diboron
ratio, which is comparable to the reaction with 2e providing 7e and reagents, which in methanol solution engage in direct aryl-boron
19e in a ratio of 63:37. However, the higher the steric hindrance on bond formation through a formal umpolung of the electrophilic
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boron center. The reaction is selective, proceeds under mild 14 (a) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60
,
conditions and does not require any metal reagent or other
promoter. It opens a new methodological venue for the use of
hypervalent diaryliodonium reagents in carbon-heteroatom bond
formation. By simply adding a palladium source, the reaction can be
directly expanded to biaryl synthesis through the cross coupling of
symmetric diaryliodonium salts.
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Financial support of this project was provided from MINECO
(CTQ2011-25027 grant to K. M., CTQ2013-43395P grant to E. F.,
Severo Ochoa Excellence Accreditation 2014-2018 to ICIQ, SEV-
2013-0319 and predoctoral FPI and FPU fellowships to N. M. and R.
M. R.), RedINTECAT CTQ2014-52974-REDC.
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