Cryptand-22 as an Efficient Ligand for the Palladium-Catalyzed Mizoroki–Heck Reaction under Air

Barahman Movassagh; Shahriar Yasham; Mozhgan Navidi

doi:10.1055/s-0033-1339897

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(20): 2671-2674
DOI: 10.1055/s-0033-1339897

letter

Cryptand-22 as an Efficient Ligand for the Palladium-Catalyzed Mizoroki–Heck Reaction under Air

Autor*innen

Barahman Movassagh*

Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Fax: +98(21)22853650 eMail: bmovass1178@yahoo.com
Shahriar Yasham

Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Fax: +98(21)22853650 eMail: bmovass1178@yahoo.com
Mozhgan Navidi

Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran Fax: +98(21)22853650 eMail: bmovass1178@yahoo.com

Abstract

Alle Artikel dieser Rubrik

Abstract

An efficient catalytic system for the Mizoroki–Heck cross-coupling reaction was developed based on the air- and heat-stable palladium(II) chloride–cryptand 22 complex. The complex is a highly active catalyst for coupling of aryl iodides, bromides, or chlorides with various olefins.

Key words

Heck reaction - cross-coupling - halides - olefins - cryptands - catalysis

Volltext

Referenzen

References and Notes

1a Beletskaya I, Cheprakov AV. Chem. Rev. 2000; 100: 3009
1b Whitcombe NJ, Hii KK, Gibson SE. Tetrahedron 2001; 57: 7449
1c Brase S, de Meijere A In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998. Chap. 3, 99
1d Reetz MT In Transition Metal Catalysed Reactions . Davies SG, Murahashi S.-I. Blackwell Science; Oxford: 1999
1e Link JT, Overman LE In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998. Chap. 6, 231
1f Crisp GT. Chem. Soc. Rev. 1998; 27: 427

2a Ren G, Cui X, Yang E, Yang F, Wu Y. Tetrahedron 2010; 66: 4022
2b Tietze LF, Ruhr W. Angew. Chem. Int. Ed. 1995; 34: 1366
2c Overman LE, Ricca DT, Tran VD. J. Am. Chem. Soc. 1993; 115: 2042

3a Shinkai I, King AO, Larsen RD. Pure Appl. Chem. 1994; 66: 1551
3b de Vries JG. Can. J. Chem. 2001; 79: 1086

4 Heck RF. Acc. Chem. Res. 1979; 12: 146

5a Hill LL, Smith JM, Brown WS, Moore LR, Guevera P, Pair ES, Porter J, Chou J, Wolterman CJ, Craciun R, Dixon DA, Shaughnessy KH. Tetrahedron 2008; 64: 6920
5b Ehrentraut A, Zapf A, Beller M. Synlett 2000; 1589
5c Böhm VP. W, Hermann WA. Chem. Eur. J. 2000; 6: 1017
5d Littke AF, Fu GC. J. Am. Chem. Soc. 2001; 123: 6989

6a Bedford RB, Welch SL. Chem. Commun. 2001; 192
6b Morales-Morales D, Redón R, Yung C, Jensen CM. Chem. Commun. 2000; 1619
6c Gibson S, Foster DF, Eastam GR, Tooze RP, Cole-Hamilton DJ. Chem. Commun. 2001; 779
6d Miyazaki F, Yamaguchi K, Shibasaki M. Tetrahedron Lett. 1999; 40: 7379

7 Yao Q, Kinney EP, Zheng C. Org. Lett. 2004; 6: 2997

8a Tsai F.-Y, Wu C.-L, Mou C.-Y, Chao M.-C, Lin H.-P, Liu S.-T. Tetrahedron Lett. 2004; 45: 7503
8b Consorti CS, Zanini ML, Leal S, Ebeling G, Dupont J. Org. Lett. 2003; 5: 983
8c Iyer S, Kulkarni GM, Ramesh C. Tetrahedron 2004; 60: 2163
8d Rocaboy C, Gladysz JA. Org. Lett. 2002; 4: 1993
8e Alonso DA, Nájera C, Pacheco MC. Adv. Synth. Catal. 2002; 344: 172

9a Yang D, Chen Y.-C, Zhu N.-Y. Org. Lett. 2004; 6: 1577
9b Bergbreiter DE, Osburn PL, Wilson A, Sink EM. J. Am. Chem. Soc. 2000; 122: 9058

10a Ma M.-T, Lu J.-M. Appl. Organomet. Chem. 2012; 26: 175
10b Demir S, Özdemir I, Cetinkaya B. Appl. Organomet. Chem. 2006; 20: 254

11 Strieter ER, Blackmond DG, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 13978
12 Collman JP, Hegedus LS, Norton JR, Finke RG. Principles and Applications of Organotransition Metal Chemistry . University Science Books; Mill Valley: 1987. 2nd ed
13 Navidi M., Movassagh B.; Monatsh. Chem. 2013, 44, 1363
14 Hsu M.-H, Hsu C.-M, Wang J.-C, Sun C.-H. Tetrahedron 2008; 64: 4268
15 Aralkenes 3; General Procedure A 5 mL round-bottomed flask was charged with aryl halide 1 (1 mmol), alkene 2 (1.1 mmol), PdCl₂–cryptand 22 (0.009 mmol, 0.9 mol%), Et₃N (1.1 mmol), and DMF (1 mL). [For aryl bromides or chlorides, TBAB (1 mmol) was also added]. The mixture was stirred at 130 °C for the appropriate time (Table 2) while the progress of the reaction was monitored (TLC). Upon completion of the reaction, the mixture was cooled to r.t., poured into H₂O (10 mL), and extracted with CH₂Cl₂ (3 × 8 mL). The combined organic extracts were washed with brine (2 × 8 mL), dried (MgSO₄), and concentrated. Purification by preparative TLC [silica gel, hexane or hexane–EtOAc (9:1)] gave the pure product. 1-Methyl-4-[(E)-2-phenylvinyl]benzene (3e) White solid; yield: 175 mg (90%); mp 119–122 °C (Lit.^2a 120–122 °C). ¹H NMR (300 MHz, CDCl₃): δ = 2.41 (s, 3 H), 7.13 (s, 2 H), 7.22 (d, J = 7.9 Hz, 2 H), 7.29 (t, J = 7.3 Hz, 1 H), 7.40 (t, J = 7.3 Hz, 2 H), 7.47 (d, J = 7.9 Hz, 2 H), 7.55 (d, J = 7.4 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 21.3, 126.45, 126.49, 127.5, 127.7, 128.65, 128.7, 129.5, 134.6, 137.55, 137.57. 1-Methyl-2-[(E)-2-phenylvinyl]benzene (3f) Pale-yellow oil; yield: 138 mg (72%). ¹H NMR (300 MHz, CDCl₃): δ = 2.51 (s, 3 H), 7.08 (d, J = 16.1 Hz, 1 H), 7.26–7.47 (m, 7 H), 7.61 (d, J = 7.6 Hz, 2 H), 7.68 (d, J = 6.5 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 20.0, 125.4, 126.3, 126.6, 126.7, 127.65, 127.69, 128.8, 130.1, 130.5, 135.9, 136.5, 137.8. 1-Methoxy-4-[(E)-2-phenylvinyl]benzene (3g) White solid; yield: 168 mg (80%); mp 136–137 °C (Lit.¹⁸ 135–137 °C). ¹H NMR (300 MHz, CDCl₃): δ = 3.85 (s, 3 H), 6.89–6.94 (m, 2 H), 6.99 (d, J = 16.3 Hz, 1 H), 7.09 (d, J = 16.3 Hz, 1 H), 7.23–7.28 (m, 1 H), 7.36 (t, J = 7.7 Hz, 2 H), 7.45–7.52 (m, 4 H). ¹³C NMR (75 MHz, CDCl₃): δ = 55.3, 114.1, 126.3, 126.6, 127.2, 127.7, 128.2, 128.7, 130.1, 137.7, 159.3. Butyl (2E)-3-(4-Methoxyphenyl)acrylate (3i) Colorless oil; yield: 200 mg (92%). ¹H NMR (300 MHz, CDCl₃): δ = 0.97 (t, J = 7.3 Hz, 3 H), 1.43 (sext, J = 7.4 Hz, 2 H), 1.70 (quin, J = 6.6 Hz, 2 H), 2.34 (s, 3 H), 4.20 (t, J = 6.6 Hz, 2 H), 6.39 (d, J = 16.0 Hz, 1 H), 7.16 (d, J = 8.0 Hz, 2 H), 7.40 (d, J = 8.0 Hz, 2 H), 7.66 (d, J = 16.0 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 13.8, 19.2, 21.4, 30.8, 64.3, 117.2, 128.0, 129.6, 131.7, 140.5, 144.5, 167.2. Butyl (2E)-3-(2-Thienyl)acrylate (3j) Pale-yellow oil; yield: 197 mg (94%). ¹H NMR (300 MHz, CDCl₃): δ = 0.96 (t, J = 7.3 Hz, 3 H), 1.43 (sext, J = 7.2 Hz, 2 H), 1.68 (quin, J = 6.8 Hz, 2 H), 4.19 (t, J = 6.6 Hz, 2 H), 6.24 (d, J = 15.7 Hz, 1 H), 7.04 (t, J = 4.9 Hz, 1 H), 7.24–7.27 (m, 1 H), 7.36 (d, J = 4.9 Hz, 1 H), 7.77 (d, J = 15.7 Hz, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 13.8, 19.2, 30.8, 64.4, 117.0, 128.1, 128.3, 130.8, 137.0, 139.6, 166.9. 4-[(E)-2-Phenylvinyl]benzonitrile (3q) White solid; yield: 168 mg (82%); mp 115–118 °C (Lit.²¹ 116–118 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.09 (d, J = 16.3 Hz, 1 H), 7.23 (d, J = 16.3 Hz, 1 H), 7.26–7.42 (m, 3 H), 7.53–7.66 (m, 6 H). ¹³C NMR (75 MHz, CDCl₃): δ = 110.6, 119.1, 126.7, 126.88, 126.94, 128.7, 128.9, 132.4, 132.5, 136.3, 141.8. 4-[(E)-2-Phenylvinyl]benzaldehyde (3r) Pale-yellow solid; yield: 176 mg (85%); mp 117–118 °C (Lit.²² 115–116 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.15 (d, J = 16.3 Hz, 1 H), 7.28 (d, J = 16.3 Hz, 1 H), 7.32–7.42 (m, 3 H), 7.56 (d, J = 7.2 Hz, 2 H), 7.66 (d, J = 7.7 Hz, 2 H), 7.88 (d, J = 7.7 Hz, 2 H), 10.0 (s, 1 H). ¹³C NMR (75 MHz, CDCl₃): δ = 126.9, 127.3, 128.5, 128.9, 130.3, 132.2, 135.3, 136.5, 143.4, 191.7. 1-{4-[(E)-2-Phenylvinyl]phenyl}ethanone (3t) Pale-yellow solid; yield: 142 mg (64%); mp 143–145 °C (Lit.²² 144–145 °C). ¹H NMR (300 MHz, CDCl₃): δ = 2.62 (s, 3 H), 7.13 (d, J = 16.3 Hz, 1 H), 7.24 (d, J = 16.3 Hz, 1 H), 7.28–7.33 (m, 1 H), 7.39 (t, J = 7.2 Hz, 2 H), 7.54 (d, J = 7.8 Hz, 2 H), 7.59 (d, J = 8.2 Hz, 2 H), 7.96 (d, J = 8.2 Hz, 2 H). ¹³C NMR (75 MHz, CDCl₃): δ = 26.6, 126.5, 126.8, 127.4, 128.3, 128.8, 128.9, 131.5, 135.9, 136.7, 142.0, 197.5.
16 Wu Y, Hou J, Yun H, Cui X, Yuan R. J. Organomet. Chem. 2001; 637–639: 793
17 Yao Q, Kinney EP, Yang Z. J. Org. Chem. 2003; 68: 7528
18 Dighe MG, Degani MS. ARKIVOC 2011; (xi): 189
19 Polshettiwar V, Hesemann P, Moreau JJ. E. Tetrahedron 2007; 63: 6784
20 Berthiol F, Feuerstein M, Doucet H, Santelli M. Tetrahedron Lett. 2002; 43: 5625
21 Sugihara T, Satoh T, Miura M, Nomura M. Adv. Synth. Catal. 2004; 346: 1765
22 Baker BR, Gibson RE. J. Med. Chem. 1971; 14: 315
23 Iranpoor N, Firouzabadi H, Tarassoli A, Fereidoonnezhad M. Tetrahedron 2010; 66: 2415
24 Gaikwad DS, Park Y, Pore DM. Tetrahedron Lett. 2012; 53: 3077