Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles

Article abstract of DOI:10.1002/chem.201000726

The palladium-catalyzed cross-coupling reaction of organogold(I) reagents (alkyl, alkenyl, aryl, and alkynyl) with organic electrophiles, such as aryl and alkenyl halides, aryl triflates, benzyl bromide, and benzoyl chloride is reported. The reaction takes place, under palladium catalysis, at room temperature with short reaction times to give the corresponding cross-coupling products in high yields.

Full text of DOI:10.1002/chem.201000726

FULL PAPER
DOI: 10.1002/chem.201000726
Palladium-Catalyzed Cross-Coupling Reactions of Organogold(I) Reagents
with Organic Electrophiles
Miguel PeÇa-Lꢀpez, Miguel Ayꢁn-Varela, Luis A. Sarandeses,* and Josꢂ Pꢂrez Sestelo*[a]
Dedicated to Professor Josꢀ Barluenga on the occasion of his 70th birthday
Abstract: The palladium-catalyzed cross-coupling reaction of organogold(I) re-
agents (alkyl, alkenyl, aryl, and alkynyl) with organic electrophiles, such as aryl
Keywords: cross-coupling · gold ·
and alkenyl halides, aryl triflates, benzyl bromide, and benzoyl chloride is report-
homogeneous catalysis · palladium ·
ed. The reaction takes place, under palladium catalysis, at room temperature with
synthetic methods
short reaction times to give the corresponding cross-coupling products in high
yields.
Introduction
we have found that organoindium compounds are also
useful reagents in metal-catalyzed cross-coupling reactions.[6]
Despite the significant number of metals that have been
tested in these reactions,[7] the utility of gold organometallics
has remained unexplored for decades. In a recent report,
Blum and co-workers showed that vinyl-gold species, inter-
mediates in a palladium-catalyzed carboauration of alkynes,
can be used in cross-coupling reactions with organic electro-
philes under palladium catalysis.[4a] Additionally, Hashmi
et al. reported the cross-coupling reaction of organogold(I)
reagents with aryl iodides.[4b] Nevertheless, important aspects
about the reactivity organogold reagents, such as their versa-
tility and the usefulness of alkylgold derivatives, still need to
be developed. In this paper we report a general study about
the reactivity of organogold(I) reagents in the palladium-
catalyzed cross-coupling reaction with different organic elec-
trophiles.
In recent years, the chemistry of gold(I) complexes has at-
tracted the attention of organic chemists due to their Lewis
acid character and their ability to stabilize cationic reaction
intermediates.[1] Nowadays, a significant number of synthetic
transformations, such as nucleophilic additions to alkynes,
alkenes, and allenes, propargylic Claisen rearrangements, cy-
cloadditions and cycloisomerizations, and reduction and oxi-
dation reactions can be performed through gold catalysis.[2]
In these transformations, carbon–gold species are transient
intermediates that can participate in further organic reac-
tions.[2,3] On the other hand, organic reactions that involve
the use of stoichiometric organogold(I) compounds are less
developed, despite the important knowledge that can be
gained for new synthetic transformations.[4]
The metal-catalyzed cross-coupling reaction of organome-
tallic reagents with organic electrophiles is one of the most
powerful reactions in organic synthesis.[5] A variety of metals
have proven to be useful, with boron (Suzuki reaction), zinc
(Negishi reaction) and tin (Stille reaction) as the most
common organometallics used. Furthermore, in recent years
Results and Discussion
Gold organometallics (RAu, R3Au) are usually unstable
compounds that require phosphines or carbenes as stabiliz-
ing donor ligands.[8] Organogold(I) compounds can be pre-
pared by transmetallation of organolithium or Grignard re-
agents and from boronic acids by using AuI salts or cationic
complexes.[9] For our study we were interested in preparing
a variety of organogold(I) compounds (aryl, alkynyl, alken-
yl, and alkyl) and we chose [Ph3PAuCl] as the gold source, a
commercially available complex soluble in the most
common organic solvents currently used in gold-catalyzed
[a] M. PeÇa-Lꢀpez, M. Ayꢁn-Varela, Prof. Dr. L. A. Sarandeses,
Prof. Dr. J. Pꢂrez Sestelo
Departamento de Quꢃmica Fundamental, Universidade da CoruÇa
Facultade de Ciencias, A Zapateira, s/n (Spain)
Fax : (+34)981-167-065
E-mail: sestelo@udc.es
qfsarand@udc.es
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/chem.201000726.
Chem. Eur. J. 2010, 16, 9905 – 9909
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reactions. Following a standard procedure,[10] the phenyl-,
phenylethynyl-, butyl-, and (E)-1-heptenylgold phosphane
reagents 1a–1d were prepared in high yields by treatment
of [Ph3PAuCl] with the corresponding organolithium re-
agents in THF at À208C (Scheme 1). These compounds
proved to be stable and could be stored at low temperature,
with the exception of 1d, which decomposed during the
workup.[11]
tone) or with lower catalyst loading (1 mol%) also provided
the cross-coupling product in similar yields and reaction
times. However, in the absence of the palladium catalyst we
did not observe any reaction.
Encouraged by these results we tested the cross-coupling
reaction of 1a with other aryl halides, such as 4-bromoaceto-
phenone (3) and the aryl triflate 4. In both cases, the palla-
dium-catalyzed reaction, carried out by using the previously
developed reaction conditions, proceeded chemoselectively
and the coupling product 6a was obtained in 87% and 93%
yield, respectively (Table 1, entries 5 and 9). These results
confirm that aryl bromides and aryl triflates are suitable
electrophiles for the cross-coupling reaction of organogold
reagents.
Following our research, we studied the reactivity of alky-
nylgold reagents. The Pd-catalyzed alkynylation is one of
the most general procedures for the synthesis of alkynes and
a gold-catalyzed Sonogashira reaction was recently report-
ed.[12] Gratifyingly, the cross-coupling reactions of phenyl-
Scheme 1. Preparation of organogold(I) reagents.
AHCTUNGTRENNUNG
With the organogold phosphanes in hand, we began our
investigation into the palladium-catalyzed cross-coupling re-
action of phenyl(triphenylphosphine)gold (1a) with aryl hal-
ides. In our first experiment, the reaction of isolated 1a
(1.1 equiv) with 4-iodotoluene (2, 1.0 equiv) in the presence
CHTUNGTRENNUNG
the catalyst, proceeded at room temperature in 1 h to afford
the arylalkynes 5b and 6b in excellent yields (84–98%,
Table 1, entries 2, 6, and 10).
At this point, we were especially interested in exploring
the reactivity of alkylgold reagents in cross-coupling reac-
tions, since, to the best of our knowledge, no report in this
area has been published to date. Surprisingly, the reaction of
butyl(triphenylphosphine)gold (1c) with 4-iodotoluene using
of [PdCl2ACHTUNGTRENNUNG(PPh3)2] (5 mol%) as the catalyst, in THF at room
temperature, afforded the cross-coupling product 5a in 99%
yield after 1 h (Table 1, entry 1). To our delight, the same
yield was obtained when the cross-coupling reaction was
performed without isolation of the organogold reagent. Ad-
ditionally, the reaction with other palladium complexes
[PdCl2ACHTNUGTRENUNG(PPh3)2] (1 mol%) as catalyst, gave 4,4’-dimethylbi-
phenyl in 92% yield at room temperature in 1 h. The reac-
tion was only observed in the presence of the palladium
complex, and the reductive homocoupling of 4-iodotoluene
can be explained by the oxidative addition of the alkyl-
([PdACHTUNGTRENNUNG(PPh3)4], [PdCl2ACHTNURTEGN(GNUN dppf)], [Pd2ACHTNUGERTN(NUGN dba)3/PPh3]; dppf=1,1’-
bis(diphenylphosphino)ferrocene, dba=dibenzylideneace-
AHCTUNGTREGgNNUN old(I) compound, although we were unable to find any
precedence for this reactivity. On the other hand, the palla-
Table 1. Palladium-catalyzed cross-coupling reaction of organogold(I) re-
agents with aryl halides and triflates.
dium-catalyzed cross-coupling reaction of 1c with 4-bromo-
AHCTUNGTREGaNNUN cetophenone (3) afforded the coupling compound 6c as a
single reaction product in a modest 30% yield (98% yield
based on recovered starting material (brsm) 3, Table 1,
entry 7). Other reaction conditions with different palladium
catalysts, such as [PdACHTUNGTRENNG(U PPh3)4] or [PdCl2ACHTUNTGNER(NUGN dppf)], at higher
temperatures, or with a larger excess of the butylgold re-
agent 1c did not improve the yield. In accordance with this
result, the treatment of 1c with aryl triflate 4 provided the
coupling product 6c in 42% yield (84% brsm, Table 1,
entry 11). Notably, the butylgold phosphane 1c remains in
the reaction mixture, which suggests that the transmetalla-
tion is the rate-determining step in the cross-coupling reac-
tion.
In a further step in the study of the reactivity of organo-
gold reagents in cross-coupling reactions, we explored the
reactivity of stereodefined alkenylgold reagents. For this
purpose we used (E)-1-heptenyl(triphenylphosphine)gold
(1d) prepared in situ from (E)-1-iodo-1-heptene (E/Z
82:18).[13] The palladium-catalyzed cross-coupling reaction
of 1d with 4-iodotoluene, under the previously developed
Entry
R
Electrophile
Product
Yield [%][a]
1
2
3
4
5
6
7
8
Ph 1a
PhC C 1b
nBu 1c
(E)-1-heptenyl 1d
Ph 1a
PhC C 1b
nBu 1c
(E)-1-heptenyl 1d
Ph 1a
PhC C 1b
2
5a
5b
5c
5d
6a
6b
6c
6d
6a
6b
6c
6d
99
98
ꢀ
[b]
–
85
87
84
3
4
ꢀ
30 (98)[c]
42 (95)[c]
93
9
ꢀ
10
11
12
86
nBu 1c
(E)-1-heptenyl 1d
42 (84)[c]
67 (95)[c]
[a] Yield of the isolated product. [b] 4,4’-Dimethylbiphenyl was isolated
in 92% yield. [c] In parentheses, the yields based on the recovered start-
ing material (brsm). OTf=trifluoromethane sulfonate.
9906
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Cross-Coupling Reactions of Organogold(I) Reagents
FULL PAPER
reaction conditions, proceeded stereospecifically at room
temperature affording the styrene 5d in 85% yield (E/Z
81:19) after 2 h with retention of the double bond configura-
tion (Table 1, entry 4).[14] The reaction using 4-bromoaceto-
phenone (3) and aryl triflate 4 as electrophiles, also afforded
the cross-coupling product 6d (E/Z 79:21) chemoselectively
in 42% and 67% yields (Table 1, entries 8 and 12). In these
cases, some of the starting electrophile was recovered and
the higher yields were obtained by using the aryl triflate 4
rather than 4-bromoacetophenone (3).
On the other hand, we also studied the cross-coupling re-
action of the organogold reagents 1a–1d with the stereode-
fined alkenyl halide b-bromostyrene (E/Z 90:10). The cross-
coupling reaction of 1a, using [PdCl2ACHTNUGTRENUNG(PPh3)2] (1 mol%) as
the catalyst at room temperature, resulted in a stereospecific
reaction affording trans-stilbene (7a) in 98% yield after 4 h
(Scheme 2). Analogously, the reaction of 1b took place in
excellent 92% yield affording the enyne 7b without isomeri-
zation (E/Z 90:10), although in this case it was necessary to
heat the reaction mixture at 758C for 2 h. In contrast to the
previous examples using 1c, the palladium-catalyzed cross-
coupling reaction of 1c with b-bromostyrene provided 7c in
72% yield without isomerization of the double bond (E/Z
92:8). In the same way, the reaction of the (E)-1-heptenyl-
Scheme 3. Palladium-catalyzed cross-coupling reaction of organogold(I)
reagents with benzyl bromide and benzoyl chloride.
isomerization. Overall, these novel results reveal organogold
reagents to be promising reagents in the benzylic coupling.
The palladium-catalyzed cross-coupling reaction of soft
organometallics with acid chlorides is a mild synthetic pro-
cedure for the preparation of ketones.[16] For this reason we
explored the reaction of phenyl-, phenylethynyl-, heptenyl-,
and butylgold phosphanes (1a–1d) with benzoyl chloride. In
all cases, the coupling reaction using only 1 mol% [PdCl2-
ACHTUNGTRENNUNG(triACHTUNGTRENNUNGphenylphosphine)gold (1d) with b-bromostyrene gave
the 1,3-diene 7d (1E,3E/1E,3Z 85:15) in 86% yield with re-
tention of the configuration in both reagents.
ACHTUNGTRENUN(NG PPh3)2] as catalyst took place efficiently at room tempera-
ture in 1 h, giving rise to the corresponding ketones 9a–9d
in high yields (88–97%, Scheme 3). Nevertheless, in the ab-
sence of a palladium catalyst the coupling reaction was not
observed.
Conclusion
We have shown that aryl, alkynyl, alkenyl, and alkylgold(I)
reagents participate in palladium-catalyzed cross-coupling
reactions with different organic electrophiles, such as aryl
and alkenyl halides, aryl triflates, benzoyl chloride, and
benzyl bromide. The cross-coupling reaction can be per-
formed under mild conditions, at room temperature and in
short reaction times, by using the isolated or the preformed
organogold reagent. The stability of the organogold phos-
phanes and their high versatility and efficiency with all the
electrophiles tested is remarkable. These results show orga-
nogold(I) phosphanes as useful reagents in cross-coupling
reactions and as valuable intermediates in organic synthesis.
Scheme 2. Palladium-catalyzed cross-coupling reaction of organogold(I)
reagents with b-bromostyrene.
At this stage, we were intrigued about the reactivity of or-
ganogold(I) reagents with other useful organic electrophiles
in cross-coupling reactions, such as benzyl halides and acid
chlorides. Benzyl halides are particularly interesting alkyl
electrophiles in cross-coupling reactions since they readily
undergo oxidative addition and do not suffer b-hydride
elimination. The cross-coupling reaction of 1a (1.1 equiv)
with benzyl bromide and [PdCl2ACTHNUTRGNEUNG(PPh3)2] (1 mol%) as the
catalyst afforded diphenylmethane (8a) in 60% yield, as a
side product we observed the formation of biphenyl
(Scheme 3). Alternatively, the reaction using 1b afforded
the coupling product 8b in quantitative yield after 4 h at
room temperature. This result is particularly interesting,
since other organometallics have failed in the benzyl-alkynyl
cross-coupling-type reaction.[15] Additionally, the reaction of
the alkenylgold phosphane 1d also provided the cross-cou-
pling product 8d (E/Z 80:20) in 83% yield without alkene
Experimental Section
General: Unless otherwise is stated, all reactions were conducted in
flame-dried glassware under a positive pressure of argon. Reaction tem-
peratures refer to external bath temperatures. Anhydrous THF was ob-
tained by distillation from the sodium/benzophenone. All other commer-
cially available reagents were used as received. Organic extracts were
dried over anhydrous MgSO4, filtered, and concentrated by using a
rotary evaporator at aspirator pressure (20–30 mmHg). TLC was carried
Chem. Eur. J. 2010, 16, 9905 – 9909
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9907

L. A. Sarandeses, J. Pꢂrez Sestelo et al.
out on silica gel 60 F254 (layer thickness 0.2 mm) and components were
located by observation under UV light and/or by treating the plates with
a phosphomolybdic acid, or p-anisaldehyde reagent followed by heating.
Column chromatography was performed on silica gel (230–400 mesh).[17]
NMR spectra were performed in a Bruker Avance 300 spectrometer
using the residual solvent signal as internal standard. DEPT spectroscopy
was used to assign carbon types. The low resolution EIMS were mea-
sured on a Thermo Finnigan Trace MS spectrometer at 70 eV. The
HRMS were measured on a Thermo Finnigan MAT 95XP spectrometer.
IR spectra were taken with a Bruker Vector 22 and with ATR (“attenu-
ated total reflectance”).
action. Alternatively, 1d can be prepared from (E)-1-heptenylboronic
acid: Cs2CO3 (105.4 mg, 0.323 mmol) and [Ph3PAuCl] (80 mg,
0.161 mmol) were added successively to a solution of (E)-1-heptenylbor-
onic acid (45.9 mg, 0.323 mmol) in dry isopropyl alcohol (5 mL). The re-
sultant white suspension was stirred at 508C for 24 h and taken to dry-
ness by rotary evaporation. The solid was extracted with benzene, filtered
through Celite, concentrated in vacuo to dryness, washed with pentane
and dried. The solid was re-extracted with a minimum of benzene, fil-
tered, washed with pentane and dried under high vacuum, to give orga-
nogold phosphane 1d as a pale brown solid (80.7 mg, 0.145 mmol, 90%).
M.p. 91–938C; 1H NMR (300 MHz, C6D6, 258C): d=0.87 (t, 3J (H,H)=
7.2 Hz, 3H), 1.26–1.49 (m, 4H), 1.61–1.71 (m, 2H), 2.56 (q, 3J (H,H)=
6.9 Hz, 2H), 6.43–6.56 (m, 1H), 6.85–6.97 (m, 9H), 7.35–7.43 (m, 6H),
7.53 ppm (dd, 3J (H,H)=18.4, 5.1 Hz, 1H); 13C NMR (75 MHz, C6D6,
General procedure for the preparation of organogold compounds: A
25 mL round-bottomed flask furnished with a stirrer bar was charged
with [Ph3PAuCl] (75 mg, 0.152 mmol) and a positive argon pressure was
established. Dry THF (3 mL) was added and the resulting solution was
cooled to À208C. A solution of RLi (1.0–2.3m in hexanes, THF or Bu2O,
0.182 mmol) was added dropwise, the mixture was stirred for 20 min, the
cooling bath was removed, and the reaction mixture stirred for 1 h at RT.
The solvent was evaporated under reduced pressure and benzene (5 mL)
was added. The mixture was filtered through Celite, concentrated in
vacuo to dryness, washed with pentane and dried. The solid was re-ex-
tracted with a minimum of benzene, filtered, washed with pentane and
dried under high vacuum.
1
258C): d=14.0 (CH3), 22.8 (2ꢅCH2), 30.2 (CH2), 31.7 (CH2), 128.7 (d, J
(C,P)=10.5 Hz, CH), 130.5 (CH), 131.7 (d, 1J (C,P)=47.2 Hz, C), 134.2
(d, 1J (C,P)=13.8 Hz, CH), 144.4 (CH), 146.4 ppm (CH); 31P NMR
(121.5 MHz, C6D6, 258C): d=45.41 ppm (s). IR (ATR): n˜ =3053, 2952,
2916, 2849, 1583, 1479 cmÀ1
.
General procedure for the palladium-catalyzed cross-coupling reaction:
A solution of [Ph3PAuR] (1.1 equiv), freshly prepared in situ by reaction
of RLi (1.1 equiv) with [Ph3PAuCl] (1.1 equiv) at À208C and warming to
RT for 1 h, was added to a mixture of the electrophile (1.0 equiv) and
palladium catalyst (1 mol%) in dry THF (4 mL). The resulting mixture
was stirred at RT under argon until the starting material had been con-
sumed (TLC). The reaction mixture was concentrated under reduced
pressure and Et2O (20 mL) was added. The ethereal phase was washed
with aqueous HCl (5%, 10 mL), brine (10 mL), dried with MgSO4, fil-
tered, and concentrated to a reduced volume under vacuum. The residue
was purified by flash chromatography to afford, after concentration and
high-vacuum drying, the corresponding cross-coupling product.
Phenyl(triphenylphosphine)gold (1a):[4c] Following the general proce-
dure, 1a was isolated as a white powder (74.8 mg, 0.139 mmol, 92%).
M.p. 160–1618C; 1H NMR (300 MHz, C6D6, 258C): d=6.88–6.97 (m,
9H), 7.26 (t, 3J (H,H)=7.4 Hz, 1H), 7.37–7.44 (m, 6H), 7.52 (t, 3J
(H,H)=7.5 Hz, 2H), 8.11 ppm (d, 3J (H,H)=7.0 Hz, 2H); 13C NMR
(75 MHz, C6D6, 258C): d=125.9 (s, CH), 127.5 (s, C), 127.7 (s, C), 127.7
1
1
(brs, CH), 128.7 (d, J (C,P)=10.5 Hz, CH), 130.6 (br s, CH), 134.2 (d, J
(C,P)=13.9 Hz, CH), 140.0 ppm (s, CH); 31P NMR (121.5 MHz, C6D6,
258C): d=43.99 ppm (s); IR (ATR): n˜ =3051, 3006, 2922, 2851, 1571,
1478, 1434 cmÀ1; MS (70 eV): m/z (%): 536 (71) [M+], 459 (100) [M+
ÀC6H5]; HRMS (EI): m/z: calcd for C24H20PAu: 536.0963 [M+]; found:
536.0944.
Acknowledgements
2-Phenylethynyl(triphenylphosphine)gold (1b):[18] Following the general
procedure, a solution of phenylethynyllithium was prepared from phenyl-
acetylene (20 mL, 0.182 mmol) and nBuLi (80 mL, 2.3m in hexanes,
0.182 mmol) using a literature procedure.[6a] The product 1b was isolated
We are grateful to the Xunta de Galicia (INCITE08PXIB103167PR) and
Ministerio de Ciencia e Innovaciꢀn (CTQ2009-07180) for financial sup-
port. M.P.L. thanks Ministerio de Ciencia e Innovaciꢀn for an FPU pre-
doctoral fellowship.
as
a white powder (84.3 mg, 0.150 mmol, 99%). M.p. 161–1628C;
1H NMR (300 MHz, C6D6, 258C): d=6.84–6.98 (m, 9H), 7.02–7.08 (m,
3H), 7.19–7.26 (m, 6H), 7.84 ppm (d, J=7.9 Hz, 2H); 13C NMR
(75 MHz, C6D6, 258C): d=126.1 (s, CH), 127.5 (s, C), 127.8 (s, C), 128.1
[1] For leading references in gold chemistry, see: a) D. J. Gorinand,
F. D. Toste, Nature 2007, 446, 395–403; b) A. Fꢆrstner, P. W. Davies,
Angew. Chem. 2007, 119, 3478–3519; Angew. Chem. Int. Ed. 2007,
46, 3410–3449; c) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180–
3211.
1
1
(d, J (C,P)=12.2 Hz, CH), 128.8 (d, J (C,P)=11.2 Hz, CH), 129.9 (s, C),
130.6 (s, C), 130.8 (d, J (C,P)=2.2 Hz, CH), 132.4 (s, CH), 134.1 ppm (d,
1
1J (C,P)=13.9 Hz, CH); 31P NMR (121.5 MHz, C6D6, 258C): d=
41.98 ppm (s); IR (ATR): n˜ =3053, 2923, 2357, 1595, 1483, 1435,
1331 cmÀ1; MS (70 eV): m/z (%): 560 (18) [M+], 459 (1) [M+ÀC8H5], 404
(100); HRMS (EI): m/z : calcd for C26H20PAu: 560.0963 [M+]; found:
560.0985.
Butyl(triphenylphosphine)gold (1c):[19] Following the general procedure,
1c was isolated as a colorless oil (64.7 mg, 0.125 mmol, 83%). 1H NMR
(300 MHz, CDCl3, 258C): d=0.97 (t, J=7.3 Hz, 3H), 1.43–1.55 (m, 4H),
1.82–1.96 (m, 4H), 7.42–7.59 ppm (m, 15H); 13C NMR (75 MHz, CDCl3,
258C): d=14.3 (s, CH3), 29.5 (d, 1J (C,P)=5.3 Hz, CH2), 30.8 (d, 1J
(C,P)=94.9 Hz, CH2), 34.1 (d, 1J (C,P)=3.8 Hz, CH2), 128.9 (d, 1J
(C,P)=10.3 Hz, CH), 130.7 (d, 1J (C,P)=2.1 Hz, CH), 131.8 (d, 1J
(C,P)=45.1 Hz, C), 134.3 ppm (d, 1J (C,P)=13.7 Hz, CH); 31P NMR
(121.5 MHz, CDCl3, 258C): d=46.37 ppm (s); IR (ATR): n˜ =3640, 2952,
2914, 2867, 1479, 1434, 1381 cmÀ1; MS (70 eV): m/z (%): 516 (7) [M+],
487 (15) [M+ÀC2H5], 459 (100) [M+ÀC4H9]; HRMS (EI): m/z: calcd for
C22H24PAu: 516.1276 [M+]; found: 516.1251.
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procedure, a solution of (E)-1-heptenyllithium, prepared from (E)-1-
iodo-1-heptene (40.8 mg, 0.182 mmol, E/Z 82:18) and tBuLi (0.215 mL,
1.7m in pentane, 0.364 mmol), was added to a solution of [Ph3PAuCl]
(90 mg, 0.182 mmol) in THF (3 mL) and the resulting organogold phos-
phane 1d was used directly in the palladium-catalyzed cross-coupling re-
9908
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Cross-Coupling Reactions of Organogold(I) Reagents
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1
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[11] The organogold phosphane 1d can be prepared and isolated from
the commercial (E)-1-heptenylboronic acid, see the Experimental
Section.
Received: March 23, 2010
Published online: June 16, 2010
Chem. Eur. J. 2010, 16, 9905 – 9909
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www.chemeurj.org
9909