Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides: Via C-C bond activation

Article abstract of DOI:10.1039/c9sc03245b

The first successful example of deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved through Ru(ii)-catalyzed C-C bond activation. The excellent chemoselectivity and broad substrate scope render this method a practical and versatile approach for the preparation of (hetero)aryl and alkenyl substituted furans, which are valuable units in many biologically active compounds and functional materials. A preliminary mechanistic study reveals that this process involves a deacylative α-ruthenation to generate key alkyl Ru(ii) intermediates with the release of a benzoic acid fragment.

Full text of DOI:10.1039/c9sc03245b

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DOI: 10.1039/C9SC03245B
ARTICLE
Ruthenium(II)-catalyzed chemoselective deacylative annulation of
,3-diones with sulfoxonium ylides via C–C bond activation
1
Received 00th January 20xx,
Accepted 00th January 20xx
Si Wen, Weiwei Lv, Dan Ba, Jing Liu, and Guolin Cheng*
DOI: 10.1039/x0xx00000x
The first successful example of deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved through Ru(II)-
catalyzed C−C bond activation. The excellent chemoselectivity and broad substrate scope render this method a practical
and versatile approach for the preparation of (hetero)aryl and alkenyl substituted furans, which are valuable units in many
biologically active compounds and functional materials. A preliminary mechanistic study reveals that this process involves
a deacylative α-ruthenation to generate the key alkyl Ru(II) intermediate with release of a benzoic acid fragment.
practical and mild synthetic approach to substituted furans,9
which are essential structural moieties in many biologically
active compounds, natural products, and functional
Introduction
Carbon−carbon bonds are the most extensive and basic
chemical bonds in organic molecules. The selective cleavage of
C−C bonds in a constructive manner enables the reconstitution
of the molecular skeleton and introduction of new functional
groups, thus attracting great attention. In the past decade,
the chemoselective C−C(CO) bond cleavage has been
1
0
materials.
a) Transition metal-catalyzed C-H functionalization/retro-Claisen condensation
O
O
O
O
O
1
Cu, Ag or Fe
H2O
R1
R2
R1
R2
R1
FG
functionalization
retro-Claisen
FG
extensively studied by employing the strategies of chelation
FG = OR, SR, PO(R)2, or CH2CN
assistance,2 ring-strain release, and aromatization-driven.
3
4
b) Deacylative C-C cupration/cross-coupling
However, the selective cleavage of unstrained C−C(CO)
O
O
CuI
O
O
+
Ar
I
CuIII
Ar
moieties without an auxiliary directing group still remains an
R1
R1
R1
R2
Ar
unmet challenge5
,6
Recently, transition metal-catalyzed
C−C(CO) bond functionalization of 1,3-diones have been
c) This work: deacylative C-C ruthenation/annuation
achieved by Jiao,6a Bolm, Peng, and Wu. These methods
6b
6c
6d
R4
R3
O
O
O
O
O
S
RuII
RuIV R4
are understood to proceed through oxidative α-
functionalization of 1,3-diones, followed by retro-Claisen
condensation to provide α-substituted ketones (Scheme 1a).
However, Lei’s work demonstrated an alternative reaction
pathway for the C−C(CO) bond cleavage of 1,3-diones, in which
the deacylative α-cupration could occur to form alkyl Cu(III)
complexes that subsequently underwent cross-coupling to give
+
R1
R1
R2
R3
R1
O
R4
R3
O
Scheme 1 Transition metal-catalyzed C−C bond activation of 1,3-diones.
On the other hand, sulfoxonium ylides are readily available
and bench-stable carbene precursors, which have been
extensively explored for the transition metal-catalyzed
7
α-aryl ketones (Scheme 1b). Inspired by Lei’s work, we
1
1
functionalization of C−H bonds. However, sulfoxonium ylide
carbene-involved C−C bond functionalization has not yet been
realized due to the challenging to control the chemoselectivity
questioned whether this open shell deacylative α-cupration
mechanism might be translated to other transition metal, such
as ruthenium, thereby delivering a catalytic formation of alkyl
Ru intermediates that can be capture by suitable coupling
partners. In continuation of our research on C−C(CO) bond
1
2
from the same starting materials.
8
cleavage reactions, herein we disclose the first ruthenium-
Results and discussion
catalyzed deacylative annulation of 1,3-diones with
sulfoxonium ylides (Scheme 1c). This method provides a
We initiated our investigation on the model reaction of 1,3-
diphenylpropane-1,3-dione (1a) with sulfoxonium ylide (2a) to
optimize various reaction parameters. The results are
summarized in Table 1. With [RuCl
catalyst, MesCO H being an additive, and Na
a. College of Materials Science & Engineering, Huaqiao University, Xiamen 361021,
China. E-mail: glcheng@hqu.edu.cn
2
(p-cymene)]
2
being a
2
3
PO being a base,
4
†
Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any the desired reaction did occur in HFIP to afford the desired
supplementary information available should be included here]. See
furan product (3aa) in 23% yield (entry 1). However, the C−H
DOI: 10.1039/x0xx00000x
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Journal Name
Table 1 Selected optimization studiesa
(entry 19). Finally, in the absence of a catalyst, no desired
product was observed (entry 20). Then, the optimized reaction
View Article Online
DOI: 10.1039/C9SC03245B
O
O
[
RuCl2(p-cymene)]2
conditions were identified, as follows: 1a (0.1 mmol), 2a (2
equiv), [RuCl (p-cymene)] (5 mol %), MesCO Li (1.5 equiv) in
Ph
R
Ph
base, MesCO2H
solvent, air, 110 °C, 24 h
O
O
R
O
R
1
a
Ph
2
2
2
Ph
R
+
Ph
Ph
O
+
Ph
+
O
o
O
O
S
R = 2-MeOC6H4
O
toluene (2 mL) at 120 C under air for 24 h (entry 18).
3aa
O
5a
4
a
With the optimal conditions in hand, we turned our
attention to the scope of 1,3-diones for this transformation
(Scheme 2). It was found that the 1,3-diones bearing methyl, -
methoxy, -halogen, and -CF groups all could be smoothly
3
carried out to afford the substituted furan products in
2a
Yield (%)b
Entry
Solvent
Base
3
aa
4a+5a (4a:5a)
45 (1:6)
8 (1:3)
20 (1:3)
14 (1:2)
24 (1:5)
trace
trace
trace
trace
0
1
2
3
4
5
6
7
8
9
HFIP
PrOH
DMF
CH CN
3
DCE
Na
3
PO
3
PO
3
PO
3
PO
3
PO
3
PO
2
CO
4
23
26
30
25
15
35
30
20
25
24
52
72
10
i
Na
Na
Na
Na
Na
Na
4
4
4
4
4
3
moderate to good yields (3aa−ao). The structure of (3ak) was
1
3
unambiguously verified by single-crystal X-ray diffraction.
The reactivity of this transformation was significantly
influenced by the steric hindrance. For 1,3-diones with ortho-
substituted phenyl rings (3al−ao) generally given lower yields
of desired products than those with meta- and para-
substituents (3ab−af). The electronic properties of the phenyl
rings on 1,3-diones were observed to affect the reaction
efficiency obviously. The substrates with electron-withdrawing
groups (3ad−af, 3ah, 3ai, and 3ak) given higher yields than
those with electron-donating groups (3ab, 3ac, and 3ag).
However, lower yield was observed when 1,3-dione with a
bromo group was used (3aj). It was noteworthy that furan and
thiophene ring were also tolerated, giving the desired products
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
toluene
K
Cs
2
CO
CO
NaHCO
KH PO
3
2
3
1
1
1
1
0
1
2
3
3
2
4
0
t
BuOLi
-
BuOLi
trace
0
c
t
1
1
6
7c,e
4
5
trace
71
78
40
85(82)
0
c
MesCO
MesCO
MesCO
MesCO
MesCO
MesCO
2
2
2
2
2
2
Li
Li
Li
Li
Li
Li
trace
trace
trace
trace
trace
0
c,d
1
1
1
1
in moderate yields (3ap, 3aq), which could be expected to find
8c,d,f
9c,d,h
0c,d,i
g
10b,14
wide applications in organic electronics.
Finally, this
66
0
reaction was not applied to pentane-2,4-dione (3ar).
2
O
O
S
[RuCl (p-cymene)]2 (5 mol %)
2
MeO
a
O
O
Reaction conditions: except where otherwise noted, all of the reactions were
performed with 1a (0.1 mmol), 2a (0.2 mmol), base (0.15 mmol), MesCO H (0.15
(5 mol %) in solvent (1 mL) at 110 °C under air for
MesCO Li (1.5 equiv)
2
+
R
R
R
O
3
2
toluene, air, 120 °C, 24 h
OMe
mmol), and [RuCl
2
CH
2
(p-cymene)]
2
1
2a
b
1
4 h. The yields were determined by H NMR analysis of the crude product using
c
d
Br
2 2
as the internal standard. without of MesCO
2
f
H. Reaction was carried out
MeO
MeO
MeO
e
at 120 °C. Reaction was carried out at 130 °C. 2 mL of toluene was used.
O
O
O
g
Isolated yield. h3 mL of toluene was used. Without [RuCl
,1,1,3,3,3-hexafluoro-2-propanol. DMF = N,N-dimethylformamide. DCE = 1,2-
dichloroethane. MesCO H = 2,4,6-trimethylbenzoic acid.
i
Me
MeO
2
2
(p-cymene)] . HFIP =
3
aa, 82%
3ab 64%
3ac, 48%
MeO
1
2
MeO
MeO
O
O
O
1
2a,b
carbene insertion product (4a)
insertion product (5a)
and the C−C carbene
F
Cl
F3C
1
2b,c
3ad, 75%
MeO
3ae, 60%
3af, 76%
were also obtained as an inseparable
mixture in 45% combined yield with 1:6 chemoselectivity.
Investigations on various solvents indicated that toluene
performed better than others, affording (3aa) in a yield of 35%
with excellent chemoselectivity (Table 1, entries 1−6). The use
of a proper base was crucial for this reaction, and the
exploration of different bases revealed that BuOLi provided
the best yield of 72% (entries 7−12). Only 10% yield of (3aa)
was obtained in the absence of a base (entry 13). The
MeO
Cl
MeO
Me
F
O
O
O
3ag, 63%
3ah
,
76%
MeO
3ai, 70%
MeO
Me
MeO
Br
F3C
O
O
O
t
3
aj, 37%
3ak, 79%
MeO
3al, 53%
OMe
MeO
F
Cl
MeO
O
O
O
MesCO
2
H additive was proved necessary to ensure the
H, trace of (3aa)
3
am, 32%
3an
3ao
generation of (3aa). In the absence of MesCO
2
,
56%
MeO
, 61%
MeO
was observed (entry 14). A comparative yield was observed
Li was used instead of BuOLi and MesCO
entry 15). The yield of (3aa) could be improved to 78% when
MeO
t
when MesCO
2
2
H
Me
O
O
O
O
S
(
3
ap, 40%
3aq, 60%
3ar, 0%
the reaction was run at elevated temperature (entry 16).
However, lower yield was obtained when the reaction was
carried out at 130 C (entry 17). Excitedly, when the solvent MesCO Li (0.15 mmol), and [RuCl (p-cymene)] (5 mol%) in toluene (2 mL) at 120 °C
Scheme 2 Scope of 1,3-diones. Reaction conditions: 1 (0.1 mmol), 2a (0.2 mmol),
o
2
2
2
was increased to 2 mL, the desired product (3aa) was obtained under air for 24 h.
in 85% yield (entry 18), but when the solvent was further
increased to 3 mL, the yield of (3aa) was reduced to 66%
2
| J. Name., 2012, 00, 1-3
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ARTICLE
indispensable moieties for the successful formation of the
R2
View Article Online
O
O
S
[RuCl2(p-cymene)]2 (5 mol %)
MesCO2Li (1.5 equiv)
R1
R1
corresponding furans, and the sulfo
DO
xoni
I
:
10
um
.1039
y
/
lide
C
9SC
s
03
w
245B
ith
O
O
Ph
+
O
3
Ph
Ph
R2
alkanoyl groups failed to provide the desired products (3cb
and 3cc).
toluene, air, 120 °C, 24 h
1a
2
Me
PhO
F
O
Ph
Ph
Ph
Ph
Ph
Ph
Ph
standard conditions
O
O
O
O
O
OMe
a)
1a
g (4.5 mmol)
+
2a
(9 mmol)
3aa
0.686 g, 61%
+
48 h
3bc, 53%
3bd, 60%
1
3
3
ba, 42%
3bb, 73%
F3C
6
, 13%
Cl
Me
OMe
MeO
Ph
Ph
O
Ph
Ph
standard conditions
48 h
O
O
O
b)
c)
1d
+
2a
O
F
1
.3 g (5.0 mmol) (10 mmol)
be, 42%
3bf, 47%
3bg, 52%
3bh, 38%
3
ad, 0.890 g, 66%
O
O
F
Cl
Br
CF3
standard conditions
O
OMe
Ph
Ph
Ph
Ph
OH
2a
O
O
O
O
+
3
bi, 37%
3bj, 47%
3bk, 56%
3bl, 63%
7
6, 25%
O
O
O
Ph
Ph
standard conditions
no reaction
O
O
O
O
+
H2O
(2 equiv)
Me
tBu
OPh
OMe
d)
e)
Ph
Ph
Ph
3
bm, 51%
3bn, 52%
3bo, 45%
3bp, 55%
1a
8, 0%
O
Ph
R
Ph
Ph
Ph
Ph
O
O
O
standard conditions
no reaction
O
Cl
Br
CF3
O
Ph
F
O
O
3
br, 51%
3bs, 44%
3bt, 53%
3
bq, 58%
OMe
R = MeO, 3aa,0%
5
a:4a = 6:1
R = H,
3ba, 0%
O
Ph
Ph
Ph
Ph
O
O
O
O
O
Ph
Ph
standard conditions
no reaction
f)
Ph
Ph
Ph
3bw, 45%
3bx, 54%
O
3
bu, 60%
3bv, 34%
O
9
3ba, 0%
Ph
S
MeO
Ph
Ph
Ph
Ph
Ph
R
O
O
O
O
O
O
standard conditions
standard conditions
R=Me, 3cb, 0%
R= Bu, 3cc, 0%
g)
h)
+
2a
2a
O
3
by, 55%
3bz, 27%
3ca, 27%
t
Ph
Ph
R
R
R = H,
3aa, trace
R = MeO, 3ac, 35%
OMe
1
s
MeO
O
O
Scheme 3 Scope of sulfoxonium ylides. Reaction conditions: 1a (0.1 mmol), 2 (0.2
mmol), MesCO Li (0.15 mmol), and [RuCl (p-cymene)] (5 mol%) in toluene (2 mL) at
20 °C under air for 24 h.
+
O
2
2
2
1
1t
CF3
R = H, 3aa, 35%
R = CF3, 3af, 32%
Next, we further investigated the reaction of 1,3-
Scheme 4 Gram-scale reactions and control experiments.
diphenylpropane-1,3-dione with a variety of aroyl sulfoxonium
ylides under the optimal reaction conditions (Scheme 3).
Various valuable functional groups were tolerated, such as
methyl, phenyl, phenoxyl, methoxyl, halogen, and
trifluoromethyl. The reactivity was not sensitive to the steric
hindrance and electronic properties of the phenyl rings on the
sulfoxonium ylides. For the ortho-position of phenyl ring,
having electron-donating moieties (3ba−bc) and electron-
withdrawing groups (3bd−bf), gave the desired products in
moderate to good yields. The substrates with meta- and para-
substituted phenyl ring could be smoothly converted into the
desired products in moderate yields (3bg−bt). Then, a phenyl
group was introduced in the para-position which formed the
tetra(aryl ring)-containing product (3bu) in 60% yield. In
addition, 1-naphthalenyl (3bv), 2-naphthalenyl (3bw), 2-furyl
A gram-scale experiment of this deacylative annulation was
demonstrated employing (1a) and (2a) as model substrates;
the product (3aa) was obtained in 61% yield, along with an
isocoumarin byproduct (6) (Scheme 4a). The 5 mmol scale
experiment of (1d) and (2a) could give the product (3ad) in
6
6% yield (Scheme 4b). Ackermann recently reported a
Ru(II)/Ag(I)-catalyzed C−H activation/annulation of benzoic
acids with sulfoxonium ylides for the synthesis of
1
1f
isocoumarins. Indeed, we notice that isocoumarin (6) could
also be generated in our silver-free conditions in 25% yield
from benzoic acid (7) and (2a) (Scheme 4c). These results
indicated that benzoic acid might be generated during the C−C
bond cleavage process.
To further understand the reaction mechanism, the reaction
of 1,3-dione (1a) and H O was investigated under the standard
2
(
3bx), and 2-thienyl (3by) substrates were also tolerated,
giving the corresponding products in the yields of 34%, 45%,
4%, and 55%, respectively. Importantly, triphenyl substituted
reaction conditions. No reaction was observed, which
indicated that the Ru(II)-catalyzed C−C activation could not
occur in the absence of a sulfoxonium ylide (Scheme 4d).
Furthermore, the mixture of 5a and 4a (6:1) could not afford
furan products (3aa or 3ba) under the standard reaction
conditions (Scheme 4e). To rule out the possibility that Paal–
Knorr furan synthesis is involved in our transformation, we
5
furan (3bz) could also be obtained using α-phenyl sulfoxonium
ylide as substrate, albeit in low yield due to the increased
bulkiness. Alkenoyl sulfoxonium ylide was also a capable
substrate, giving 2-alkenyl substituted furan (3ca) in 27% yield.
The aryl/alkenyl groups in conjugation with the carbonyl are
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
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Journal Name
also prepared 1,4-diphenylbutane-1,4-dione (9); however, no
desired product (3ba) was obtained when this 1,4-dione was
subjected to the standard reaction conditions (Scheme 4f).
Finally, the intramolecular competitive reactions of
unsymmetrical 1,3-diones (1s) or (1t) with (2a) indicated that
the chemoselectivity of this reaction was affected by the
electron density of aryl-group, and the C–C bond cleavage tend
to occur at the less electron-rich moieties (Scheme 4g and 4h).
The electron-deficient carbonyls are more likely to be attacked
Acknowledgements
View Article Online
DOI: 10.1039/C9SC03245B
This work was supported by the NSF of China (21672075), the
Program for New Century Excellent Talents in Fujian Province
University, and the Instrumental Analysis Center of Huaqiao
University.
Notes and references
1
For selected reviews, see: (a) B. Rybtchinski and D. Milstein,
Angew. Chem. Int. Ed., 1999, 38, 870; (b) C.-H. Jun, Chem.
Soc. Rev., 2004, 33, 610; (c) M. Murakami and T. Matsuda,
Chem. Commun., 2011, 47, 1100; (d) M. A. Drahl, M.
Manpadi and L. J. Williams, Angew. Chem. Int. Ed., 2013, 52,
2
by a nucleophile, such as H O, which may induce the
subsequent C–C bond cleavage.
On the basis of these results, we proposed that the reaction
would proceed as showed in the Scheme 5. The
transformation begins with the generation of Ru complex (A)
under basic condition, which is subsequently captured by
sulfoxonium ylide to form Ru carbene complex (B). Then, the
1
1
1
1222; (e) F. Chen, T. Wang and N. Jiao, Chem. Rev., 2014,
14, 8613; (f) T. Wang and N. Jiao, Acc. Chem. Res., 2014, 47,
137; (g) P.-h. Chen, B. A. Billett, T. Tsukamoto and G. Dong,
ACS Catal., 2017, 7, 1340; (h) P. Sivaguru, Z. Wang, G. Zanoni
and X. Bi, Chem. Soc. Rev., 2019, 48, 2615. For selected
examples, see: (i) M. Gozin, A. Weisman, Y. Bendavid and D.
Milstein, Nature, 1993, 364, 699; (j) J. Zhu, J. Wang and G.
Dong, Nat. Chem., 2019, 11, 45.
C−C bond activation occurs in the presence of H
complex (C). Migratory insertion of (C) affords intermediate
D). Finally, intramolecular annuation of (D) results in
2
O, giving Ru
(
intermediate (E), following by β-O elimination to finish the
furan products (3) and regenerate the Ru(II) catalyst.
2
(a) A. M. Dreis and C. J. Douglas, J. Am. Chem. Soc., 2009,
1
31, 412; (b) J. Wang, W. Chen, S. Zuo, L. Liu, X. Zhang and J.
Wang, Angew. Chem. Int. Ed., 2012, 51, 12334; (c) Z.-Q. Lei,
H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, J. Sun and Z.-J. Shi,
Angew. Chem. Int. Ed., 2012, 51, 2690; (d) Y. Xia, G. Lu, P. Liu
and G. Dong, Nature, 2016, 539, 546; (e) D.-S. Kim, W.-J. Park
and C.-H. Jun, Chem. Rev., 2017, 117, 8977; (f) Y. Xia, J. Wang
and G. Dong, J. Am. Chem. Soc., 2018, 140, 5347; (g) T.-T.
Zhao, W.-H. Xu, Z.-J. Zheng, P.-F. Xu and H. Wei, J. Am. Chem.
Soc., 2018, 140, 586.
(a) L. Souillart and N. Cramer, Chem. Rev., 2015, 115, 9410;
(b) G. Fumagalli, S. Stanton and J. F. Bower, Chem. Rev.,
2017, 117, 9404; (c) L. Deng, M. Chen and G. Dong, J. Am.
Chem. Soc., 2018, 140, 9652.
R4
O
O
R1
HBase
R2
+
H O
R1
R3
2
1
O
3
RuII
HBase
+
O
Base
4
R Ru
OH
R3
Ru
O
R1
ligands on Ru were omitted
R2
R1
O
A
E
O
O
S
3
R3
R4
2
DMSO
4
5
Y. Xu, X. Qi, P. Zheng, C. C. Berti, P. Liu and G. Dong, Nature,
2019, 567, 373.
O
O
R1
Ru
R4
Ru
R1
R3
O
O
R4
R3
For examples on transition metal-catalyzed oxidative
cleavage of unstrained C–C(CO) bonds, see: (a) L. Zhang, X.
Bi, X. Guan, X. Li, Q. Liu, B.-D. Barry and P. Liao, Angew.
Chem. Int. Ed., 2013, 52, 11303; (b) X. Huang, X. Li, M. Zou, S.
Song, C. Tang, Y. Yuan and N. Jiao, J. Am. Chem. Soc., 2014,
R2
O
D
B
H2O
O
O
Ru
2
R1
R3
R CO2H
C
R4
1
36, 14858; (c) A. Maji, S. Rana, Akanksha and D. Maiti,
Angew. Chem. Int. Ed., 2014, 53, 2428; (d) C. Tang and N.
Jiao, Angew. Chem. Int. Ed., 2014, 53, 6528; (e) N. Vodnala,
R. Gujjarappa, C. K. Hazra, D. Kaldhi, A. K. Kabi, U. Beifuss
and C. C. Malakar, Adv. Synth. Catal., 2019, 361, 135.
Scheme 5 Plausible catalytic cycle.
Conclusions
6
(a) C. Zhang, P. Feng and N. Jiao, J. Am. Chem. Soc., 2013,
1
35, 15257; (b) L.-H. Zou, D. L. Priebbenow, L. Wang, J.
In conclusion, we have demonstrated the first example of
Ru(II)-catalyzed chemoselective deacylative annulation of 1,3-
diones with sulfoxonium ylides. A series of substituted furans
have been synthesized in reasonable yields from this novel
method. This protocol that use of unstrained C−C(CO) bond as
nucleophiles in transition metal-catalyzed cross couplings
should be expected to find wide implications. More work to
better understand the mechanistic information of this strategy
is currently underway
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Conflicts of interest
There are no conflicts to declare.
9
For selected examples on furan synthesis, see: (a) R. C. D.
Brown, Angew. Chem. Int. Ed., 2005, 44, 850; (b) S. F. Kirsch,
Org. Biomol. Chem., 2006, 4, 2076; (c) A. V. Gulevich, A. S.
4
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Chemical Science
Page 6 of 6
Table of Contents
View Article Online
DOI: 10.1039/C9SC03245B
[
RuCl (p-cymene)] (5 mol %)
2 2
R4
O
O
O
O
S
MesCO Li (1.5 equiv)
2
+
R3
R1
R3
R1
R2
toluene, air, 120 °C, 24 h
O
R4
4
6 examples, up to 82% yield
The highly chemoselective Ru(II)-catalyzed deacylative annulation of
,3-diones with sulfoxonium ylides was achieved to deliver (hetero)aryl
substituted furans.
1