Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes

Article abstract of DOI:10.1039/c8ob00630j

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph₃PAu^IR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

Full text of DOI:10.1039/c8ob00630j

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
benzene
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Gold(I)-Catalyzed Cross-Coupling Reactions of Aryldiazonium Salts
with Organostannanes
Manjur O. Akram,ab Popat S. Shinde,ab Chetan C. Chintawarc and Nitin T. Patilc*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Abstract.
Gold(I)-catalyzed
cross-coupling
reactions
of reductive elimination of gold(III) species. Unfortunately, the
aryldiazonium salts with organostannanes is described. This redox oxidation of LAuIX to [LAuIIIArX2] by ArN2X is reported to be
neutral strategy offers an efficient approach to diverse biaryls, vinyl achievable only under harsh reaction conditions.10 To circumvent
arenes and arylacetylenes. Monitoring the reaction with NMR and this limitation, we mulled over organo-stannanes which reportedly
ESI-MS provided strong evidence for the in situ formation of have the ability to undergo transmetalation with various gold-
Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the species11 to form organo-gold precursors. Based on these
activation of aryldiazonium salts.
reports10,11 and our interest in the field of oxidative gold catalysis,12
we envisaged that aryltrialkylstannanes would generate catalytically
active organo-gold(I) species A which would poised to undergo
oxidation by aryldiazonium salts to generate [AuIII] intermediate B
which after reductive elimination would give cross-coupled
products (Scheme 1c). Be noted that the Sn/Au transmetalation has
been well-documented in the Pd-catalyzed Stille cross-coupling
reactions;13 however, to the best of our knowledge, it has never
been employed in gold-catalyzed cross-coupling reactions. Herein,
we report gold(I)-catalyzed cross-coupling reactions of
aryldiazonium salts with organostannanes under redox neutral
conditions to access diverse biaryls, vinyl arenes, and arylacetylenes
at ambient conditions.
Oxidative gold catalysis is emerging as a powerful tool for a
variety of C–C and C–X bond-forming reactions since last few years.1
However, unlike the late transition metals, reports on analogues
gold-catalyzed cross-coupling reactions are scarce.1e,2 The reason
could be attributed to higher redox potential between Au(I) and
Au(III) species.3,2b Recent research revealed that the realization of
Au(I)/Au(III) redox cycle is possible with two-electron redox
processes; however, those reactions utilize sacrificial oxidants such
as I3+ derivatives or F+ sources4 and often require harsh reaction
conditions. To facilitate advancement in the field of oxidative gold
catalysis, the development of new mode of reactivity is highly
warranted.
Very recently, the research groups of Glorius,5 Toste,6 Hashmi7
and others8 have disclosed entirely new concept for gold-catalyzed
cross-coupling reactions. Rather than involving external oxidants,
the method employs aryl radicals (generated in situ via light-
mediated decomposition of aryldiazonium salts, ArN2X) which acts
as both oxidant and coupling partner in an overall redox-neutral
transformation (Scheme 1a). The research group of Shi achieved an
alternative photo-free approach to trigger gold(I) oxidation via
ligand/nucleophile-assisted activation of diazonium salts (Scheme
1b).9 We wondered whether it would be possible to develop a gold-
catalyzed cross-coupling reaction that would eliminate the need of
either light or nucleophile for diazonium activation.
We thought of generating organo-gold(I) species in situ which
Scheme 1. Mode of oxidation of gold(I)-precursors by aryldiazonium
salts: known and present work
can be oxidized by ArN2X leading to the cross-coupled product after
At the outset, we studied the coupling reaction of 4-
(ethoxycarbonyl)benzenediazonium tetrafluoroborate (1a) and
tributyl(phenyl)stannane (2a) in the presence of various Au(I)-
catalysts.14 The main challenge was the suppression of undesired
homodimerization product which could results either from 1a or
2a. The optimum reaction conditions for obtaining the desired
aDivision of Organic Chemistry, CSIR - National Chemical Laboratory, Dr. Homi
Bhabha Road, Pune - 411 008, India.
bAcademy of Scientific and Innovative Research (AcSIR), New Delhi - 110 025, India.
cDepartment of Chemistry, Indian Institute of Science Education and Research
Bhopal, Bhauri, Bhopal - 462 066, India. Email: npatil@iiserb.ac.in
Supporting information for this article is given via
a link at the end of the
document. Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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product 3a in higher yield (69%) is treating 1a with 2a in the salts was examined. As can be judged from Table 2 that the
presence of 7 mol% Ph3PAuCl in CH3CN (Scheme 2).
substituent at the para-position of the aryl ring in
tributyl(aryl)stannanes (-tBu, -CF3 and -CN) were tolerated giving
3aa-3ac in 61-66% yields. However, lowering of yield was noticed in
case of electron donating 4-OMe group (3ad, 39%). Changing
substituents (-Cl, -OMe and -3,5-di-CF3) at the meta-position didn’t
affect the outcome of the reaction (3ae-3ag, 59-71% yields). Ortho-
substituted aryl stannanes, on the contrary, furnished the
corresponding coupled products 3ah-3aj in poor yields (24-42%).
Further, compounds 3ak and 3al were accessed in 74 and 56%
yields. Heteroaromatic(aryl)stannanes also provided the
corresponding coupling products 3am-3ao in moderate yields (43-
56%). Relatively bulky tributyl(3-methylbenzofuran-2-yl)stannane
provided the desired product 3ap in 31% yield along with undesired
3ap' in 16% yield. The reaction also worked well with aryldiazonium
salts with varying counter ions. For instance, cross coupled products
3a was accessed in 66% (X = PF6), 70% (X = OCOCF3) and 77% (X =
OTs) yields.
Scheme 2. Optimized reaction conditions
As shown in Table 1, the reaction is found to have worked well
with a broad range of substituted aryldiazonium salts (1). For
example, aryldiazonium salts containing -Br and -Ph substituents at
the para-position, gave the corresponding cross-coupled products
3b and 3c in 48 and 46% yields, respectively. Interestingly, electron-
withdrawing substituents such as -COMe, -CO2Me, -CN and -NO2
provided 3d-3g in slightly better yields (49-62% yields). However, in
case of electron donating substituent such as 4-OMe and 3,4-
methylenedioxy, the products 3h and 3v were obtained in low
yields (40 and 31% yields).6a,8h,j Notably, aryldiazonium salts bearing
4-ethynyl group provided the product 3i in 37% yield. In the case of
substituents at the ortho-position of the diazonium salts both
electronic and steric factors seemed to play a crucial role. For
example, -Br and -I substituent at the ortho-position of the
diazonium salt led to the formation of 3j and 3k in 41% and 50%
yields, respectively. Further, electron withdrawing substituent such
as -COMe and -NO2 provided coupling products (3l and 3m) in
better yields (50 and 51%); whereas, electron donating substituents
-OMe led to poor conversion (3n, 31%). The reaction of ArN2BF4
bearing o-Et, o-iPr and 2,4,6-trimethyl groups in the aryl ring gave
3o, 3p and 3w in lower yields; probably because of the steric
reasons.6a,8j On the contrary, substituents at the meta-position of
aryl ring in ArN2BF4 were tolerated affording 3q-3u in moderate
yields (42-62%). Further, 1-phenylnaphthalene 3x was also accessed
in 41% yield. The scope of the reaction was further extended to
quinoline and indole based heteroaryls to obtain 3y and 3z in 19
and 56% yields, respectively.
Table 2. Scope with respect to tributyl(aryl)stannanes (2) and
counteranions of the aryldiazonium saltsa
N2X
+
R
SnBu3
Ph3PAuCl (7 mol%)
R
CH3CN (0.1 M), N2
16 h, rt
EtO2C
EtO2C
3aa, R = 4-tBu, 66%
3ab, R = 4-CF3, 61%
3ac, R = 4-CN, 61%
1
2
3
EtO2C
3ae, R = 3-Cl, 71%
3af, R = 3-OMe, 64%
3ag, R = 3,5-di CF3, 59%
3ah, R = 2-CN, 42%
3ai
R
EtO2C
X
3am, X = O, 54%
3an, X = N-Boc, 43%
3ao, X = S, 56%
, R = 2-OMe, 24%b
3aj, R = 2,4,6-tri Me, 25%
Me
3ak, R = 1-anthracenyl, 74%
3al, R = 2-anthracenyl, 56%
3ad, R = 4-OMe, 39%
EtO2C
Ph
O
3a, 66%, for X = PF6
3a, 70%, for X = O(CO)CF3
3a, 77%, for X = OTs
Me
3ap, 31%
N
N
O
EtO2C
3ap , 16%
CO2Et
aReaction conditions: 0.20 mmol 1, 0.26 mmol 2, 7 mol% Ph3PAuCl,
degassed CH3CN (0.1 M), N2, rt, 16 h. bNMR yields using
dibromomethane as an internal standard.
Table 1. Cross-coupling reactions of ArN2BF4 (1) with PhSnBu3 (2a)a
Very interestingly, vinyl-tributyltin was also found to be
tolerated giving 3aq-3as; albeit, in poor yields (Table 3). However,
electron
deficient
vinyl-stannnane-ethyl-(Z)-3-
(tributylstannyl)acrylate provided better results (3at, 58%; 3au,
67%; 3av, 53% and 3aw, 55%). Notably, Z-selectivity is retained in
all the cases. Next, C(sp2)-C(sp) coupling reactions employing
tributyl(ethynyl)stannane were investigated. Reaction of
aryldiazonium salts bearing electron withdrawing/donating groups
(4-CO2Et, 4-NO2, 4-OMe and 3-CN) gave 3ax-3aaa in 42-68% yields.
However, aryldiazonium salts bearing substituents at the ortho-
position afforded products with low yields (3aab, 47%; 3aac, 44%;
3aad, 35%; 3aae, 36%). Interestingly, diazonium salts bearing very
labile TMS-acetylene group provided 3aaf in 29% yield. Further, 2-
ethynyl naphthalene (3aag) was accessed in 57% yield. Employing
tributyl(phenylethynyl)stannane, unsymmetrical alkynes 3aah and
3aai were also accessed in 41 and 33% yields, respectively.
Unfortunately, alkyl-stannanes such as allyltributylstannane and
aReaction conditions: 0.20 mmol 1, 0.26 mmol 2a, 7 mol%
Ph3PAuCl, degassed CH3CN (0.1 M), N2, rt, 16 h. NMR yields using
b
dibromomethane as an internal standard.
Next, the scope of the reaction with respect to various
tributyl(aryl)stannanes (2) and counteranions of the aryldiazonium
2 | J. Name., 2012, 00, 1-3
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benzyltributylstannane failed to provide C(sp2)-C(sp3) coupled competitive radical chain mechanism (path c) cannot be ruled out
products 3aaj and 3aak.
completely.5c,2d
Table 3. Cross-coupling reactions of aryldiazonium salts with vinyl,
ethynyl and alkyl-stannanesa
N2BF4
Ph3PAuCl (7 mol%)
R
+
R
SnBu3
Ar
Ar
CH3CN (0.1 M), N2
16 h, rt
1
2
3
R
R
CO2Et
3as, 31%b
N
3aq, R = 3-NO2, 27%b
3ar, R = 4-NO2, 24%b
3at, R = 4-I, 58%
3au, R = 3-CN, 67%
3av, R = 3-CF3, 53%
3aw, 55%
CO2Et
N
R
R
Ph
TMS
3ax, R = 4-CO2Et, 52%
3ay, R = 4-NO2, 68%
3az, R = 4-OMe, 42%
3aaa, R = 3-CN, 57%
3aab, R = 2-Br, 47%
3aac, R = 2-I, 44%
3aaf, 29%
3aah, R = 4-NO2, 41%
3aai, R = 4-OMe, 33%
R
3aaj, R = allyl, -%c
, R = benzyl, -%c
EtO2C
3aak
3aad, R = 2-CN, 35%
3aae, R = 2-OPh, 36%
3aag, 57%
aReaction conditions: 0.20 mmol 1, 0.26 mmol 2, 7 mol% Ph3PAuCl,
Scheme 3. Control experiments
c
degassed CH3CN (0.1 M), N2, rt, 16 h. bReaction kept for 4 h. No
reaction.
Next, the reaction of 1a and 2a under optimized reaction
conditions was monitored with 31P NMR spectroscopy (Scheme 3a).
We found the complete disappearance of Ph3PAuICl (δ 32.9 ppm)
with the appearance of new signal at δ 44.2 ppm (after 5 min) and δ
22.9 ppm (after 16 h) which were assigned as Ph3PAuIPh (II)8c and
X1/X2,6a,15 respectively. The presence of X1 and X2 was further
confirmed by HRMS analysis.14 Notably, these species were not
observed in appreciable amount in the 31P NMR spectrum as a large
excess of stannane 2a (1.3 equiv) was employed. To gain further
evidence on the plausible intermediates, 1aa was treated with 2a
under standard reaction conditions (Scheme 3b). HRMS analysis of
the reaction mixture taken after 10 min revealed the peak at m/z =
690.1606 which corresponds to the X3.14 The detection of
intermediates X3 along with X1 and X2 clearly implies the
involvement of Au(III)-intermediate via the oxidation of gold(I)-
precursors. Further, when 1a was reacted with 2a in the presence
of preformed Ph3PAuIPh (II) as a catalyst, 3a was obtained in 51%
yield (Scheme 3c). This observation clearly indicates the
intermediacy of Ph3PAuIPh species (II) along with the fact that the
reaction is proceeding via the transmetalation/oxidation sequence.
A control experiment outlined in Scheme 3d clearly ruled out the
intermediacy of azo-compound (3ap') as possible intermediate.9b
Scheme 4. A proposed catalytic cycle
Conclusions
In conclusion, we have developed a method for cross-coupling
reactions of aryldiazonium salts with various oragnostannanes to
access diverse array of biaryls, vinyl arenes, and arylacetylenes
under gold(I) catalysis. This reaction proceeds under very mild
conditions involving Au(I)/Au(III) redox cycle and showing excellent
functional group tolerance which may be difficult to exhibit under
conventional Pd-catalysis.
Mechanistically,16 the catalyst Ph3PAuCl would first undergo
transmetalation with PhSnBu3 (2a) to generate Ph3PAuIPh (II). A
process involving two-electron oxidative addition with diazonium
salt would then convert Ph3PAuIPh (II) into the transient gold(III)-
species III.9a The gold-species III then collapses to intermediate V
Conflicts of interest
via rapid transmetalation/N2 extrusion sequence either in
a
There are no conflicts to declare.
concerted manner (path a) or in a stepwise manner (path b).15,17
Further, intermediate V would undergo fast reductive elimination17
to yield the desired 3a (along with 3a').2d However, at present, a
Acknowledgements
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Generous financial support by the Department of Science and
Technology (DST), New Delhi (grant number SB/S1/OC-17/2013),
EMR/2014/001235 is gratefully acknowledged. M.O.A. and P.S.S.
thanks CSIR for the award of Senior Research Fellow-ship. C.C.C.
thanks UGC for the award of Junior Research Fellowship.
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