6
of 7
PIERROT ET AL.
+
13
+
2
H), 7.81 (d, J = 8.9 Hz, 2H), 2.09 (s, 4H), 0.84 (s, 6H).
C
(C). HRMS (ESI+): [M + H ] calcd for C H BrO
23 16 3
NMR (101 MHz, C D ) δ 175.8 (C), 168.2 (C), 162.9 (C),
419.0277, found 419.0274.
6
6
1
49.6 (C), 141.3 (C), 140.0 (C), 129.8 (2CH), 123.1
Methods and results of the theoretical studies are
detailed in the Supporting Information.
(2CH), 117.8 (C), 43.97 (C), 40.68 (CH ), 37.08 (CH ),
2
2
+
2
9.44 (2CH ). HRMS (ESI+): [M + H ] calcd for
3
+
C H NO 302.1023, found 302.1023.
16
16
5
ACKNOWLEDGMENTS
Product 4d: Following the general procedure, the
reaction between diazodimedone (17 mg, 0.10 mmol)
Financial support from the Agence Nationale de la
3
and the sulfur ylide 3 with R = 4‐MeO‐C H (21 mg,
Recherche
(ANR‐13‐JS07‐0002‐01),
Aix‐Marseille
6
4
0
.10 mmol) afforded the furan 4d (28 mg, quant.) as a yel-
Université, Centrale Marseille, and the Centre National
de la Recherche Scientifique (CNRS) is gratefully
acknowledged. We thank the Centre Régional de Compé-
tences en Modélisation Moléculaire (Aix‐Marseille
Université) for computing facilities.
low oil. The NMR analyses revealed the presence of an
unidentified impurity in ca. 15%. H NMR (400 MHz,
C D ) δ 8.50 (d, J = 9.0 Hz, 2H), 6.76 (d, J = 9.0 Hz,
1
6
6
2
H), 3.20 (s, 3H), 2.14 (s, 2H), 2.11 (s, 2H), 0.85 (s, 6H).
13
C NMR (101 MHz, C D ) δ 178.4 (C), 165.7 (C), 163.1
6
6
(
C), 161.5 (C), 141.3 (C), 131.6 (2CH), 117.4 (C), 113.7
ORCID
(2CH), 54.5 (CH ), 43.9 (C), 40.7 (CH ), 37.3 (CH ), 29.6
3
2
2
+
+
(2CH ). HRMS (ESI+): [M + H ] calcd for C H O
3
17 19
4
2
87.1278, found 287.1276.
Product 4e: Following the general procedure, the
reaction between 2‐diazo‐cycloheptan‐1,3‐dione (18 mg,
0
3
.10 mmol) and the sulfur ylide 3 with R = 4‐Br‐C H
6
4
(
26 mg, 0.10 mmol) afforded the furan 4e (32 mg,quant.)
REFERENCES
1
as a yellow oil. H NMR (400 MHz, C D ) δ 8.09 (d,
J = 8.6 Hz, 2H), 7.28 (d, J = 8.6 Hz, 2H), 2.15 (t,
J = 5.8 Hz, 2H), 2.03 (t, J = 6.0 Hz, 2H), 1.28‐1.14 (m,
4
1
6
6
[
1] Reviews: a)C. Wentrup, W. Heilmayer, G. Kollenz, Synthesis
994, 1219. b) G. Kollenz, S. Ebner, in Science of Synthesis:
1
13
Houben‐Weyl Methods of Molecular Transformations, (Ed: R.
Danheiser) Vol. 23, Georg Thieme Verlag, Stuttgart, Germany
H). C NMR (101 MHz, C D ) δ 178.3 (C), 162.8 (C),
6 6
58.7 (C), 135.4 (C), 134.6 (C), 131.6 (2CH), 130.8
2006 271. c) K. P. Reber, S. D. Tilley, E. J. Sorensen, Chem. Soc.
(2CH), 111.9 (C), 23.6 (CH ), 21.9 (CH ), 21.6 (CH ),
2 2 2
+
Rev. 2009, 38, 3022. d) A. Ford, H. Miel, A. Ring, C. N. Slattery,
A. R. Maguire, M. A. McKervey, Chem. Rev. 2015, 115, 9981.
1
8.5 (CH ). HRMS (ESI+): [M + H ] calcd for
2
+
3
C H BrO 321.0121, found 321.0122.
15
14
[2] a) J. A. Hyatt, P. L. Feldman, R. J. Clemens, J. Org. Chem. 1984,
Product 4f: Following the general procedure, the reac-
tion between α‐diazoacetylacetone (13 mg, 0.10 mmol)
4
9, 5105. b) R. Cookson, T. N. Barrett, A. G. M. Barrett, Acc.
Chem. Res. 2015, 48, 628.
3
and the sulfur ylide 3 with R = 4‐Br‐C H (26 mg,
6
4
[3] Reviews: a)W. Kirmse, Eur. J. Org. Chem 2002, 2193. b) Y.
Coquerel, J. Rodriguez, in Molecular Rearrangements in Organic
Synthesis, (Ed: C. Rojas), Wiley, Hoboken 2015, Chap. 3 59.
0
.10 mmol) afforded the furan 4f (29 mg, quant.) as a yel-
1
low oil. H NMR (400 MHz, C D ) δ 8.05 (d, J = 8.6 Hz,
6
6
2
H), 7.27 (d, J = 8.5 Hz, 2H), 1.60 (s, 3H), 1.58 (s, 3H).
C NMR (101 MHz, C D ) δ 178.4 (C), 163.2 (C), 155.0
[
4] For representative recent work: a)M. Presset, Y. Coquerel, J.
Rodriguez, J. Org. Chem. 2009, 74, 415. b) M. Presset, Y.
Coquerel, J. Rodriguez, Org. Lett. 2010, 12, 4212. c) M. Presset,
K. Mohanan, M. Hamann, Y. Coquerel, J. Rodriguez, Org. Lett.
2011, 13, 4124. d) J. Galvez, J.‐C. Castillo, J. Quiroga, M.
Rajzmann, J. Rodriguez, Y. Coquerel, Org. Lett. 2014, 16,
13
6
6
(C), 134.9 (C), 134.6 (C), 131.5 (2CH), 130.8 (2CH),
1
09.32 (C), 29.71 (s), 11.80 (CH ), 5.43 (CH ). HRMS
3
3
+
+
(ESI+): [M + H ] calcd for C H BrO 294.9964, found
13 12 3
2
94.9964.
Product 4g: Following the general procedure, the
reaction between 2‐diazo‐1,3‐diphenyl‐propane‐1,3‐dione
4126. e) P. Neupane, L. Xia, Y. R. Lee, Adv. Synth. Catal.
2014, 356, 2566. f) J.‐C. Castillo, J. Quiroga, J. Rodriguez, Y.
Coquerel, Eur. J. Org. Chem. 2016, 1994.
3
(26 mg, 0.10 mmol) and the sulfur ylide 3 with R = 4‐
[
[
[
5] D. Pierrot, M. Presset, J. Rodriguez, D. Bonne, Y. Coquerel,
Chem. A Eur. J. 2018, 24, 11110.
Br‐C H4 (26 mg, 0.10 mmol) afforded the furan 4g
6
1
(42 mg, quant.) as a yellow oil. H NMR (400 MHz,
6] Y. Dudognon, M. Presset, J. Rodriguez, Y. Coquerel, X. Bugaut,
T. Constantieux, Chem. Commun. 2016, 52, 3010.
C D ) δ (d, J = 8.6 Hz, 2H), 7.56‐7.51 (m, 2H), 7.51‐7.44
6
6
13
(m, 2H), 7.25 (d, J = 8.6 Hz, 2H), 7.14‐6.96 (m, 6H).
C
7] Recent reviews on sulfur ylides and their (4 + 1) annulations:
a)L.‐Q. Lu, T.‐R. Li, Q. Wang, W.‐J. Xiao, Chem. Soc. Rev.
NMR (101 MHz, C D ) δ 180.1 (C), 161.0 (C), 152.9 (C),
6
6
1
(
1
35.5 (C), 134.5 (C), 131.7 (2CH), 130.8 (2CH), 129.8
C), 129.6 (2CH), 129.6 (CH), 129.5 (C), 128.7 (2CH),
28.5 (2CH), 128.2 (CH), 127.3 (2CH), 125.32 (C), 115.71
2017, 46, 4135. b) J.‐R. Chen, X.‐Q. Hu, L.‐Q. Lu, W.‐J. Xiao,
Chem. Rev. 2015, 115, 5301. c) C. Zhu, Y. Ding, L.‐W. Ye, Org.
Biomol. Chem. 2015, 13, 2530.