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Organic & Biomolecular Chemistry
Page 11 of 14
Journal Name
DOI: 10.1039/C7OB01466J
ARTICLE
acetate (4.5 mg, 0.02 mmol, 0.1 equiv), thiophene-3-
carbaldehyde (26 µL, 0.3 mmol, 1.5 equiv), and aq. tert-butyl
hydroperoxide (82 µL, 0.6 mmol, 3.0 equiv). Column
chromatography (SiO2, eluting with 7:3 hexane/ethyl acetate)
afforded the desired product as a colourless oil, (30.0 mg,
56%). 1H NMR (600 MHz, CDCl3): δ 8.46 (d, J = 4.2 Hz, 1H), 7.77
(d, J = 7.2 Hz, 1H), 7.58-7.62 (m, 4H), 7.52 (t, J = 7.2 Hz, 1H),
7.49 (d, J = 7.8 Hz, 1H), 7.42 (d, J = 4.8 Hz, 1H), 7.15-7.16 (m,
1H), 7.07-7.09 (m, 1H); 13C NMR (150 MHz, CDCl3): δ 191.8,
157.0, 149.2, 142.8, 140.0, 139.4, 136.3, 133.9, 130.3, 129.2,
128.7, 128.4, 127.6, 125.8, 122.9, 121.9; IR (neat): υmax 1656,
1586, 1428, 1273, 858, 752 cm-1; HRMS (ESI, m/z) calcd. for
C16H11NSONa [M + Na]+: 288.0459; found: 288.0460.
C. Berk and J. Talbert, J. Org. Chem., 1988, 53, 2392-2394. (d)
E. Negishi, V. Bagheri, S. Chatterjee, F. T. Luo, J. A. Miller and
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5
6
(a) L. Liebeskind and J. Srogl, J. Am. Chem. Soc., 2000, 122
11260-11261. b) P. Zurer, Chem. Eng. News, 2000, 78, 26.
,
(a) A. Brennführer, H. Neumann and M. Beller, Angew. Chem.
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Chen, Tetrahedron Lett., 2001, 42, 175-177.
7
(a) F. Liao, R. Shi, Y. Sha, J. Xia, W. Liao and A. Lei, Chem.
Commun., 2017, 53, 4354-4357. (b) B. Manji, D. Kundu, T.
Ghosh and B. C. Ranu, Adv. Synth. Catal. 2016, 358, 283-295.
(c) X. Wu, Y. Zhao and H. Ge, J. Am. Chem. Soc., 2015, 137
,
4924-4927. (d) B. Zhao, M. Yu, H. Liu, Y. Chen, Y. Yuan and X.
Xie, Adv. Synth. Catal. 2014, 356, 3295-3301. (e) S. Guin, S. K.
Rout, A. Banerjee, S. Nandi and B. K. Patel, Org. Lett., 2012,
14, 5294-5297. (f) H. Wang, L.-N. Guo and X.-H. Duan, Org.
Lett., 2012, 14, 4358-4361. (g) J. Park, E. Park, A. Kim, Y. Lee,
K.-W. Chi, J. H. Kwak, Y. H. Jung and I. S. Kim, Org. Lett., 2011,
13, 4390-4393. (h) F. Xiao, Q. Shuai, F. Zhao, O. Baslé, G.
Deng and C.-J. Li, Org. Lett., 2011, 13, 1614-1617. (i) T. Kochi,
3-Methyl-1-(2-(pyridin-2-yl)phenyl)but-2-en-1-one,
3as,
Scheme 4. The same general procedure was followed by using
2-phenylpyridine (31.0 mg, 0.2 mmol, 1.0 equiv), palladium(II)
acetate (4.5 mg, 0.02 mmol, 0.1 equiv), 3-methylbut-2-enal (29
µL, 0.3 mmol, 1.5 equiv), and aq. tert-butyl hydroperoxide (82
µL, 0.6 mmol, 3.0 equiv). Column chromatography (SiO2,
eluting with 7:3 hexane/ethyl acetate) afforded the desired
1
product as a colourless oil, (15.0 mg, 76%). H NMR (600 MHz,
A. Tazawa, K. Honda and F. Kakiuchi, Chem. Lett. 2011, 40,
CDCl3): δ 8.64 (d, J = 4.8 Hz, 1H), 7.72 (td, J = 7.8 Hz, 1.8 Hz,
1H), 7.62 (d, J = 7.2 Hz, 1H), 7.58 (d, J = 7.8 Hz, 1H), 7.52-7.54
(m, 1H), 7.46-7.48 (m, 2H), 7.22-7.24 (m, 1H), 6.03 (s, 1H), 2.08
(s, 3H), 1.72 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 196.0, 158.1,
154.8, 149.2, 142.1, 139.4, 136.1, 130.1, 129.5, 128.4, 128.1,
125.3, 123.5, 122.0, 27.5, 20.7; IR (neat): υmax 2926, 1666,
1615, 1434, 1236, 1012, 752 cm-1; HRMS (ESI, m/z) calcd. for
C16H15NONa [M + Na]+: 260.1051; found: 260.1057.
1018-1020.
8
For selected reviews, see: (a) T. Gensch, M. N. Hopkinson, F.
Glorius and J. Wencel-Delord, Chem. Soc. Rev., 2016, 45
,
2900-2936. (b) O. Tischler, B. Tóth and Z. Novák, Chem. Rec.,
2016, 17, 184-199. (c) J. Wencel-Delord, T. Drӧge, F. Liu and
F. Glorius, Chem. Soc. Rev., 2011, 40, 4740-4761. For
selected examples, see: (d) N. Xu, P. Li, Z. Xie and L. Wang,
Chem. Eur. J., 2016, 22, 2236-2242. (e) M. Shang, S.-H. Zeng,
S.-Z. Sun, H.-X. Dai and J.-Q. Yu, Org. Lett., 2013, 15, 5286-
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Houlden, C. D. Bailey, J. G. Ford, M. R. Gagné, G. C. Lloyd-
For the spectroscopy data of compounds 3ac, 3ae, 3af, 3ag,
3al, 3ao, 3aq, 3ar, 3at, 3au and 3av see the ESI.
Acknowledgements
Jones, K. I. Booker-Milburn, J. Am. Chem. Soc., 2008, 130
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10066-10067.
RJ thanks DST, SERB, Govt. of India for Ramanujan fellowship;
award no. SR/S2/RJN-97/2012 and extra mural research grant
no. EMR/2014/000469 for financial support. AH, KM and MKM
thank CSIR and UGC respectively for their fellowships.
9
For selected reviews, see: (a) W. I. Dzik, P. P. Lange and L. J.
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3
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