RSC Advances
DOI: 10.1039/C4RA15980B
(
1
(
2C), 133.1, 133.0, 131.7, 129.2, 128.8, 127.9, 127.7, 127.3 (3C),
Rev., 2008, 108, 2952–3015; (d) V. D. Bock, H. Hiemstra and J. H.
van Maarseveen, Eur. J. Org. Chem., 2006, 51–68.
5
5
27.1, 126.5, 126.4, 125.1, 76.1, 54.5, 21.3. HRMS (ESIꢀTOF)
+
2
3
(a) V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless,
Angew. Chem., Int. Ed., 2002, 41, 2596–2599; (b) C. Tornøe, C.
Christensen and M. Meldal, J. Org. Chem., 2002, 67, 3057–3064.
m/z): calcd for C H IN , [M + H] 426.0462; found 426.0458.
20 16 3
1
-(α-Methylbenzyl)-4-(4-methylphenyl)-5-iodo-1,2,3-
o
5
triazole (4s). White solid (88 mg, 45%), mp 144−146 C. IR v
(a) J. M. Schulman, A. A. Friedman, J. Panteleev and M. Lautens,
Chem. Commun., 2012, 48, 55–57; (b) M. Juricek, K. Stout, P. H. J.
Kouwer and A. E. Rowan, Org. Lett., 2011, 13, 3494–3497; (c) J.
Panteleev, K. Geyer, A. AguilarꢀAguilar, L. Wang and M. Lautens,
Org. Lett., 2010, 12, 5092–5095.
ꢀ
1 1
60
3
(
7
023, 2994, 2931, 2861, 1611, 1480, 1448, 1217 cm ; H NMR
400 MHz, CDCl3) 7.81 (d, J = 7.8 Hz, 2H), 7.36−7.29 (m, 5H),
.26−7.24 (m, 2H), 5.78 (q, J = 7.2 Hz, 1H), 2.38 (s, 3H), 2.10 (d,
δ
1
3
J = 7.2 Hz, 3H); C NMR (100 MHz, CDCl3)
138.4, 129.1 (2C), 128.8 (2C), 128.2, 127.5 (2C), 127.4, 126.6
2C), 76.6, 61.4, 22.3, 21.3. HRMS (ESIꢀTOF) (m/z): calcd for
δ 149.7, 140.2,
4
5
(a) J. S. Oakdale, R. K. Sit and V. V. Fokin, Chem. Eur. J., 2014, 20,
11101–11110; (b) Y.ꢀM. Wu, J. Deng, Y. Li and Q.ꢀY. Chen,
Synthesis, 2005, 1314–1318.
1
0
65
(
+
C H IN , [M + H] 390.0462; found 390.0466.
1
7
16
3
(a) E. Schwartz, K. Breitenkamp and V. V. Fokin, Macromolecules,
2
1
011, 44, 4735–4741. (b) A. Bogdan and K. James, Org. Lett., 2011,
3, 4060–4063; (c) J. Deng, Y.ꢀM. Wu and Q.ꢀY. Chen, Synthesis,
1
-(Oct-1-yl)-4-(4-methylphenyl)-5-iodo-1,2,3-triazole (4t).
o
Light yellow solid (179 mg, 90%), mp 72−74 C. IR v 3038,
70
2005, 2730–2738.
ꢀ
1 1
1
5
2920, 2856, 1641, 1510, 1460, 1225 cm ; H NMR (400 MHz,
CDCl3) 7.82 (d, J = 7.8 Hz, 2H), 7.27 (d, J = 7.8 Hz, 2H), 4.42
t, J = 7.3 Hz, 2H), 2.40 (s, 3H), 1.98−1.91 (m, 2H), 1.38−1.28
m, 10H), 0.88 (t, J = 6.9 Hz, 3H); C NMR (100 MHz, CDCl3)
149.7, 138.3, 129.2 (2C), 127.5, 127.3 (2C), 75.8, 50.9, 31.7,
6
(a) J. C. Morris, J. Chiche, C. Grellier, M. Lopez, L. F. Bornaghi, A.
Maresca, C. T. Supuran, J. Pouyssegur and S.ꢀA. Poulsen, J. Med.
Chem., 2011, 54, 6905–6918; (b) T. Ostrowski, P. Januszczyk, M.
Cieslak, J. KazmierczakꢀBaranska, B. Nawrot, E. Bartoszakꢀ
Adamska and J. Zeidler, Bioorg. Med. Chem., 2011, 19, 4386–4398;
δ
(
(
δ
1
3
7
8
8
9
5
0
5
0
(c) V. Malnuit, M. Duca, A. Manout, K. Bougrin and R. Benhida,
2
0
29.9, 29.0, 28.9, 26.4, 22.6, 21.3, 14.0. HRMS (ESIꢀTOF) (m/z):
calcd for C H IN , [M + H] 398.1088; found 398.1085.
Synlett, 2009, 2123–2128; (d) N. Joubert, R. F. Schinazi and L. A.
Agrofoglio, Tetrahedron, 2005, 61, 11744–11750.
+
17
24
3
7
(a) J. GarcíaꢀÁlvarez, J. Diez, J. Gimeno, F. J. Suarez and C. Vincent,
Eur. J. Inorg. Chem., 2012, 5854–5863; (b) P. Diner, T. Andersson,
J. Kjellen, K. Elbing, S. Hohmann and M. Groli, New J. Chem., 2009,
33, 1010–1016; (c) J. E. Hein, J. C. Tripp, L. B. Krasnova, K. B.
Sharpless and V. V. Fokin, Angew. Chem., Int. Ed., 2009, 48, 8018–
1
-(3-Methylbut-1-yl)-4-(4-methylphenyl)-5-iodo-1,2,3-
o
triazole (4u). White solid (163 mg, 92%), mp 83−85 C. IR v
ꢀ
1 1
3
035, 2950, 2920, 2861, 1641, 1514, 1460, 1255 cm ; H NMR
(400 MHz, CDCl3) 7.81 (d, J = 7.8 Hz, 2H), 7.27 (d, J = 7.8 Hz,
H), 4.44 (t, J = 7.8 Hz, 2H), 2.40 (s, 3H), 1.84 (q, J = 6.9 Hz,
2
5
δ
8
021.
(a) D. Fu, J. Zhang and S. Cao, J. Fluorine Chem., 2013, 156, 170–
76; (b) B. T. Worrell, J. E. Hein and V. V. Fokin, Angew. Chem.,
2
2
1
3
8
9
H), 1.73−1.66 (m, 1H), 1.01 (d, J = 8.3 Hz, 6H); C NMR (100
149.7, 138.3, 129.2, 127.5 (2C), 127.3 (2C),
6.7, 49.4, 38.6, 25.6, 22.3 (2C), 21.3. HRMS (ESIꢀTOF) (m/z):
1
MHz, CDCl3)
δ
Int. Ed., 2012, 51, 11791–11794.
7
+
(a) W. S. Brotherton, R. J. Clark and L. Zhu, J. Org. Chem., 2012,
7
V. Dzyuba, Tetrahedron Lett., 2010, 51, 550–553; (c) L. Li, G.
Zhang, A. Zhu and L. Zhang, J. Org. Chem., 2008, 73, 3630–3633.
3
0
calcd for C H IN , [M + H] 356.0618; found 356.0616.
14 18 3
7, 6443–6455; (b) N. W. Smith, B. P. Polenz, S. B. Johnson and S.
1
-Cycylohexyl-4-(4-methylphenyl)-5-iodo-1,2,3-triazole
o
(
3
4v). Light yellow solid (138 mg, 75%), mp 156−158 C. IR v
ꢀ
1
1
10 (a) C. Vidal and J. GarcíaꢀÁlvarez, Green Chem., 2014, 16, 3515–
521. (b) J. GarciaꢀÁlvarez, J. Diez and J. Gimeno, Green Chem.,
035, 2923, 2853, 1611, 1510, 1450, 1225 cm ; H NMR (400
7.81 (d, J = 7.8 Hz, 2H), 7.26 (d, J = 7.8 Hz, 2H),
4.41−4.34 (m, 1H), 2.39 (s, 3H), 2.12−1.95 (m, 6H),
3
MHz, CDCl3)
δ
2010, 12, 2127–2130.
3
5
95
11 (a) M. Nouzarian, R. Hosseinzadeh and H. Golchoubian, Synth.
Commun., 2013, 43, 2913–2925; (b) P. Starkov, F. Rota, J. M.
D’Oyley and T. D. Sheppard, Adv. Synth. Catal., 2012, 354, 3217–
1
3
1
.79−1.76(m, 1H), 1.52−1.26 (m, 3H); C NMR (100 MHz,
CDCl3) 149.1, 138.2, 129.1 (2C), 127.6, 127.5 (2C), 75.8, 61.1,
2.7 (2C), 25.4 (2C), 25.0, 21.3. HRMS (ESIꢀTOF) (m/z): calcd
δ
3
224; (c) K. R. Reddy, M. Venkateshwar, C. U. Maheswari and P. S.
3
+
Kumar, Tetrahedron Lett., 2010, 51, 2170–2173; (d) J. Yan, J. Li and
D. Cheng, Synlett, 2007, 2442–2444; (e) G. W. Kabalka and A. R.
Mereddy, Tetrahedron Lett., 2004, 45, 1417–1419; (f) F. Homsi and
G. Rousseau, Tetrahedron Lett., 1999, 40, 1495–1498; (g) H.
Monenschein, G. SourkouniꢀArgirusi, K. M. Schubothe, T. O’Hare
and A. Kirschning, Org. Lett., 1999, 1, 2101–2104; (h) D. Naskar and
S. Roy, J. Org. Chem., 1999, 64, 6896–6897; (i) Y. Brunel and G.
Rousseau, Tetrahedron Lett., 1995, 36, 2619ꢀ2622; (j) T. Jeffery, J.
Chem. Soc., Chem. Commun., 1988, 909–910.
for C H IN , [M + H] 368.0618; found 368.0618.
15
18
3
1
00
4
0
Acknowledgements
This work was supported by the National Natural Scientific
Foundation of China (Nos. 21472107, 21372142 and 21072112).
105
Notes and references
1
2. G. Pelletier, S. Lie, J. J. Mousseau and A. B. Charette, Org. Lett.,
a
Department of Chemistry, Tsinghua University, Beijing 100084, P. R.
China. Fax: +86ꢀ10ꢀ62771149; Tel: +86ꢀ10ꢀ62795380; Eꢀmail:
2
012, 14, 5464–5467. The decomposition of 1ꢀiodoalkynes was
4
5
1
1
10
15
studied and a special note was gaven in SI (pp S12ꢀS13) of this
article: “Note: The synthesized 1ꢀiodoalkynes were found usually
unstable to light exposure and trace of iodine is observed when the
product is solubilized or purified by flash chromatography (a pink
color gradually appears when flashed or stored on the bench at room
temperature). They should be kept under argon in the freezer (–20
1
13
†
Electronic Supplementary Information (ESI) available: H and
NMR spectra for products 4aꢀ4v. See DOI: 10.1039/b000000x/
C
5
0
1
For selected reviews, see: (a) N. V. Sokolova and V. G. Nenajdenko,
RSC Adv., 2013, 3, 16212–16242; (b) Applications of click chemistry
themed issue (guest eds: M. G. Finn and V. V. Fokin), Chem. Soc.
Rev., 2010, 39, 1231–1405; (c) M. Meldal and C. W. Tornøe, Chem.
°C) or use directly in a further reaction.”.
13 B. Wang, J. Zhang, X. Wang, N. Liu, W. Chen and Y. Hu, J. Org.
Chem., 2013, 78, 10519–10523.
This journal is © The Royal Society of Chemistry [year]
Journal Name, [year], [vol], 00–00 | 5