E
Synlett
G. Oss, T. V. Nguyen
Cluster
A. R. H.; Sarpong, R. Angew. Chem. Int. Ed. 2013, 52, 11129.
n) Hong, B.; Li, H.; Wu, J.; Zhang, J.; Lei, X. Angew. Chem. Int. Ed.
015, 54, 1011.
4) (a) Griffith, A. K.; Vanos, C. M.; Lambert, T. H. J. Am. Chem. Soc.
012, 134, 18581. (b) Hong, X.; Liang, Y.; Griffith, A. K.;
(14) These two catalysts did not seem to promote the intermolecu-
lar COM reaction as preliminary reactions gave unsatisfactory
outcomes.
(
2
(
(15) General Procedure A
2
A 4 mL vial was charged with NIS (10 mol%) and a stirring bar.
Starting material 1 was added to the vial under ambient atmo-
sphere, along with three drops of DCE, added to help with the
stirring of reaction mixture. The vial was closed by a cap, and
the mixture was stirred for 24 h at room temperature, unless
otherwise specified. Upon completion (as determined by TLC
analysis), the crude mixture was directly purified by flash
column chromatography, to give the metathesis products.
General Procedure B
A 4 mL vial was charged with ICl (10 mol%, as a stock solution in
DCE) and a stirring bar. Starting material 1 was added to the vial
under nitrogen atmosphere. The vial was kept under nitrogen,
and the mixture was stirred for 24 h at room temperature,
unless otherwise specified. Upon completion (as determined by
TLC analysis), the crude mixture was directly purified by flash
column chromatography, to give the metathesis products.
Lambert, T. H.; Houk, K. N. Chem. Sci. 2014, 5, 471. (c) Lambert
T. H.; Synlett; 2019, 30: in press; DOI: 10.1055/s-0039-
1
689924.
5) (a) Veluru Ramesh, N.; Bah, J.; Franzén, J. Eur. J. Org. Chem. 2015,
834. (b) Ni, S.; Franzén, J. Chem. Commun. 2018, 54, 12982.
(
(
1
6) (a) Ludwig, J. R.; Zimmerman, P. M.; Gianino, J. B.; Schindler, C.
S. Nature 2016, 533, 374. (b) Ludwig, J. R.; Phan, S.; McAtee, C.
C.; Zimmerman, P. M.; Devery, J. J.; Schindler, C. S. J. Am. Chem.
Soc. 2017, 139, 10832. (c) McAtee, C. C.; Riehl, P. S.; Schindler, C.
S. J. Am. Chem. Soc. 2017, 139, 2960. (d) Groso, E. J.; Golonka, A.
N.; Harding, R. A.; Alexander, B. W.; Sodano, T. M.; Schindler, C.
S. ACS Catal. 2018, 8, 2006. (e) Albright, H.; Vonesh, H. L.;
Becker, M. R.; Alexander, B. W.; Ludwig, J. R.; Wiscons, R. A.;
Schindler, C. S. Org. Lett. 2018, 20, 4954. (f) Ludwig, J. R.;
Watson, R. B.; Nasrallah, D. J.; Gianino, J. B.; Zimmerman, P. M.;
Wiscons, R. A.; Schindler, C. S. Science 2018, 361, 1363.
2-Methyl-3-(p-tolyl)-1-tosyl-2,5-dihydro-1H-pyrrole (2a)
1
(7) Ma, L.; Li, W.; Xi, H.; Bai, X.; Ma, E.; Yan, X.; Li, Z. Angew. Chem.
H NMR (300 MHz, CDCl ): = 7.79 (d, J = 8.3 Hz, 2 H), 7.31 (d,
3
Int. Ed. 2016, 55, 10410.
8) Catti, L.; Tiefenbacher, K. Angew. Chem. Int. Ed. 2018, 57, 14589.
9) Tran, U. P. N.; Oss, G.; Pace, D. P.; Ho, J.; Nguyen, T. V. Chem. Sci.
J = 8.0 Hz, 2 H), 7.27–7.06 (m, 4 H), 5.80 (q, J = 2.0 Hz, 1 H), 5.02
(ddddd, J = 9.0, 6.2, 4.1, 3.1, 1.7 Hz, 1 H), 4.30 (q, J = 2.5 Hz, 2 H),
2.38 (d, J = 16.9 Hz, 6 H), 1.50 (d, J = 6.4 Hz, 3 H) ppm. 13C NMR
(
(
2018, 9, 5145.
(75 MHz, CDCl ): = 143.4, 143.2, 138.1, 135.1, 130.1, 129.8,
3
(
10) Tran, U. P. N.; Oss, G.; Breugst, M.; Detmar, E.; Pace, D. P.;
Liyanto, K.; Nguyen, T. V. ACS Catal. 2019, 9, 912.
129.4, 127.3, 126.3, 117.9, 63.0, 54.8, 22.1, 21.5, 21.2 ppm.
3-(p-Tolyl)-1-tosyl-2,5-dihydro-1H-pyrrole (2b)
1
(11) (a) Breugst, M.; Detmar, E.; von der Heiden, D. ACS Catal. 2016,
H NMR (400 MHz, CDCl ): = 7.76 (d, J = 8.2 Hz, 2H), 7.35–7.26
3
6
2
, 3203. (b) Breugst, M.; von der Heiden, D. Chem. Eur. J. 2018,
4, 9187.
(m, 7 H), 5.83–5.81 (m, 1 H), 5.03–5.0 (m, 1 H), 4.30–4.28 (m, 2
H), 2.40 (s, 3 H), 1.48 (d, J = 6.0 Hz, 3 H) ppm. C NMR (100
13
(12) See the Supporting Information for more details.
MHz, CDCl ): = 143.5, 143.4, 135.1, 133.0, 129.8, 128.7, 128.2,
3
(
13) (a) Kniep, F.; Jungbauer, S. H.; Zhang, Q.; Walter, S. M.;
Schindler, S.; Schnapperelle, I.; Herdtweck, E.; Huber, S. M.
Angew. Chem. Int. Ed. 2013, 52, 7028. (b) Jungbauer, S. H.;
Walter, S. M.; Schindler, S.; Rout, L.; Kniep, F.; Huber, S. M.
Chem. Commun. 2014, 50, 6281. (c) Gliese, J.-P.; Jungbauer, S. H.;
Huber, S. M. Chem. Commun. 2017, 53, 12052. (d) Dreger, A.;
Engelage, E.; Mallick, B.; Beer, P. D.; Huber, S. M. Chem. Commun.
127.3, 126.3, 118.8, 62.9, 54.8, 22.1, 21.5 ppm.
Butyl 2-Phenylcyclopent-2-ene-1-carboxylate (2g)
1
H NMR (400 MHz, CDCl ): = 7.56–7.41 (m, 2 H), 7.41–7.11 (m,
3
3 H), 6.35 (td, J = 2.6, 1.6 Hz, 1 H), 4.13–3.90 (m, 3 H), 2.75
(dddd, J = 17.3, 8.9, 4.6, 2.6 Hz, 1 H), 2.68–2.53 (m, 1 H), 2.48–
2.14 (m, 1 H), 1.63–1.42 (m, 2 H), 1.37–1.19 (m, 2 H), 0.87 (t,
13
J = 7.3 Hz, 3 H) ppm. C NMR (100 MHz, CDCl ): = 175.3,
3
2
018, 54, 4013. (e) Schulz, N.; Sokkar, P.; Engelage, E.; Schindler,
S.; Erdelyi, M.; Sanchez-Garcia, E.; Huber, S. M. Chem. Eur. J.
018, 24, 3464. (f) Stoesser, J.; Rojas, G.; Bulfield, D.; Hidalgo, P.
141.2, 135.5, 130.0, 128.3, 127.2, 125.8, 64.4, 51.3, 32.5, 30.6,
29.3, 19.0, 13.6 ppm. IR (neat): 3055, 2960, 1726, 1457, 1383,
–1
+
2
1330 cm . HRMS: m/z calcd for [C16H20O Na] : 267.1361;
2
I.; Pasán, J.; Ruiz-Pérez, C.; Jiménez, C. A.; Huber, S. M. New J.
Chem. 2018, 42, 10476. (g) von der Heiden, D.; Detmar, E.;
Kuchta, R.; Breugst, M. Synlett 2018, 29, 1307.
found: 267.1356.
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2019. Thieme. All rights reserved. Synlett 2019, 30, A–E