SCOPUS 정보 검색 플랫폼

Volumn , Issue 9, 2008, Pages 1366-1370

Intramolecular cycloisomerization of aryl-substituted alkylidenecyclopropanes via NHC palladium-catalyzed cascade C-C bond cleavage/C-H activation/C-C bond formation

(2) Yang, Yewei a Huang, Xian a,b

a ZHEJIANG UNIVERSITY (China)

b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY (China)

Author keywords

Alkylidenecyclopropanes; Cycloisomerization; Dihydronaphthalenes; N heterocyclic carbene; Ring opening

Indexed keywords

ALKENE; CARBENE; CYCLOPROPANE DERIVATIVE; NAPHTHALENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLIZATION; ELIMINATION REACTION; ISOMERIZATION; RING OPENING; SUBSTITUTION REACTION;

EID: 45749111096 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078404 Document Type: Article

Times cited : (14)

References (61)

1
- 0001487604
- (a) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
- (1998) Chem. Rev , vol.98 , pp. 589
- Brandi, A.¹ Goti, A.²

2
- 0001500173
- (b) Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
- (2002) Adv. Synth. Catal , vol.344 , pp. 111
- Nakamura, I.¹ Yamamoto, Y.²

3
- 0038640190
- (c) Brandi, A.; Cicchi, S.; Cordera, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
- (2003) Chem. Rev , vol.103 , pp. 1213
- Brandi, A.¹ Cicchi, S.² Cordera, F.M.³ Goti, A.⁴

4
- 1642272805
- (a) Nakamura, I.; Kamada, M.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 2903.
- (2004) Tetrahedron Lett , vol.45 , pp. 2903
- Nakamura, I.¹ Kamada, M.² Yamamoto, Y.³

5
- 0035847198
- (b) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270.
- (2001) J. Org. Chem , vol.66 , pp. 270
- Camacho, D.H.¹ Nakamura, I.² Saito, S.³ Yamamoto, Y.⁴

6
- 0034701226
- (c) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 2661
- Nakamura, I.¹ Saito, S.² Yamamoto, Y.³

7
- 0000135142
- (d) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458.
- (1998) J. Org. Chem , vol.63 , pp. 6458
- Nakamura, I.¹ Itagaki, H.² Yamamoto, Y.³

8
- 0030794889
- (e) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 8123
- Tsukada, N.¹ Shibuya, A.² Nakamura, I.³ Yamamoto, Y.⁴

9
- 0029818919
- (f) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 10676
- Lautens, M.¹ Meyer, C.² Lorenz, A.³

10
- 33646576245
- (a) Fürstner, A.; Aïssa, C. J. Am. Chem. Soc. 2006, 128, 6306.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 6306
- Fürstner, A.¹ Aïssa, C.²

11
- 0034623540
- (b) Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 11015
- Suginome, M.¹ Matsuda, T.² Ito, Y.³

12
- 4344715554
- (a) Saito, S.; Masuda, M.; Komagawa, S. J. Am. Chem. Soc. 2004, 126, 10540.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 10540
- Saito, S.¹ Masuda, M.² Komagawa, S.³

13
- 0037067556
- (b) Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 4911.
- (2002) J. Org. Chem , vol.67 , pp. 4911
- Kawasaki, T.¹ Saito, S.² Yamamoto, Y.³

14
- 0030850587
- (a) Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069.
- (1997) J. Org. Chem , vol.62 , pp. 6069
- Bessmertnykh, A.G.¹ Blinov, K.A.² Grishin, Y.K.³ Donskaya, N.A.⁴ Tveritinova, E.V.⁵ Yur'eva, N.M.⁶ Beletskaya, I.P.⁷

15
- 0000776521
- (b) Chiusoli, G. P.; Costa, M.; Melli, L. J. Organomet. Chem. 1998, 358, 495.
- (1998) J. Organomet. Chem , vol.358 , pp. 495
- Chiusoli, G.P.¹ Costa, M.² Melli, L.³

16
- 0037123792
- (a) Nüske, H.; Bräse, S.; Kozhushkov, S. I.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem. Eur. J. 2002, 8, 2350.
- (2002) Chem. Eur. J , vol.8 , pp. 2350
- Nüske, H.¹ Bräse, S.² Kozhushkov, S.I.³ Noltemeyer, M.⁴ Es-Sayed, M.⁵ de Meijere, A.⁶

17
- 0035903583
- (b) Nüske, H.; Noltemeyer, M.; de Meijere, A. Angew. Chem. Int. Ed. 2001, 40, 3411.
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 3411
- Nüske, H.¹ Noltemeyer, M.² de Meijere, A.³

18
- 22144496835
- (a) Shi, M.; Wang, B.-Y.; Huang, J.-W. J. Org. Chem. 2005, 70, 5606.
- (2005) J. Org. Chem , vol.70 , pp. 5606
- Shi, M.¹ Wang, B.-Y.² Huang, J.-W.³

19
- 33745042632
- (b) Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc. 2006, 128, 7430.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 7430
- Shi, M.¹ Liu, L.-P.² Tang, J.³

20
- 26844452040
- Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. J. Org. Chem. 2005, 70, 8503.
- (2005) J. Org. Chem , vol.70 , pp. 8503
- Hadei, N.¹ Kantchev, E.A.B.² O'Brien, C.J.³ Organ, M.G.⁴

21
- 1842738116
- Arentsen, K.; Caddick, S.; Cloke, F. G. N.; Herring, A. P.; Hitchcock, P. B. Tetrahedron Lett. 2004, 45, 3511.
- (2004) Tetrahedron Lett , vol.45 , pp. 3511
- Arentsen, K.¹ Caddick, S.² Cloke, F.G.N.³ Herring, A.P.⁴ Hitchcock, P.B.⁵

22
- 0344443261
- Frisch, A. C.; Rataboul, F.; Zapf, A.; Beller, M. J. Organomet. Chem. 2003, 687, 403.
- (2003) J. Organomet. Chem , vol.687 , pp. 403
- Frisch, A.C.¹ Rataboul, F.² Zapf, A.³ Beller, M.⁴

23
- 0242407300
- (a) Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 13642
- Eckhardt, M.¹ Fu, G.C.²

24
- 0000759864
- (b) Batey, R. A.; Shen, M.; Lough, A. J. Org. Lett. 2002, 4, 1411.
- (2002) Org. Lett , vol.4 , pp. 1411
- Batey, R.A.¹ Shen, M.² Lough, A.J.³

25
- 0001273662
- (a) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
- (2001) Org. Lett , vol.3 , pp. 1511
- Yang, C.¹ Lee, H.M.² Nolan, S.P.³

26
- 0000078839
- (b) McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741.
- (2000) J. Organometallics , vol.19 , pp. 741
- McGuinness, D.S.¹ Cavell, K.²

27
- 0002442679
- (c) Herrmann, W. A.; Reisinger, C.-P.; Spiegier, M. J. Organomet. Chem. 1998, 557, 93.
- (1998) J. Organomet. Chem , vol.557 , pp. 93
- Herrmann, W.A.¹ Reisinger, C.-P.² Spiegier, M.³

28
- 0032723198
- For leading reviews on NHC, see: a
- For leading reviews on NHC, see: (a) Arduengo, A. J. III Acc. Chem. Res. 1999, 32, 913.
- (1999) Acc. Chem. Res , vol.32 , pp. 913
- Arduengo III, A.J.¹

29
- 0002138516
- (b) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
- (2000) Chem. Rev , vol.100 , pp. 39
- Bourissou, D.¹ Guerret, O.² Gabbaï, F.P.³ Bertrand, G.⁴

30
- 0037090932
- (c) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1290
- Herrmann, W.A.¹

31
- 6044274718
- (d) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5130
- Nair, V.¹ Bindu, S.² Sreekumar, V.³

32
- 0038614445
- (a) Huang, X.; Zhou, H. Org. Lett. 2002, 4, 4419.
- (2002) Org. Lett , vol.4 , pp. 4419
- Huang, X.¹ Zhou, H.²

33
- 0242320438
- (b) Zhou, H.; Huang, X.; Chen, W. Synlett 2003, 13, 2080.
- (2003) Synlett , vol.13 , pp. 2080
- Zhou, H.¹ Huang, X.² Chen, W.³

34
- 0842264137
- (c) Huang, X.; Zhou, H.; Chen, W. J. Org. Chem. 2004, 69, 839.
- (2004) J. Org. Chem , vol.69 , pp. 839
- Huang, X.¹ Zhou, H.² Chen, W.³

35
- 3543013732
- (d) Zhou, H.; Huang, X.; Chen, W. J. Org. Chem. 2004, 69, 5471.
- (2004) J. Org. Chem , vol.69 , pp. 5471
- Zhou, H.¹ Huang, X.² Chen, W.³

36
- 34248376986
- (e) Huang, X.; Yang, Y. Org. Lett. 2007, 9, 1667.
- (2007) Org. Lett , vol.9 , pp. 1667
- Huang, X.¹ Yang, Y.²

37
- 1942456891
- Lebel, H.; Janes, M. K.; Charette, A. B.; Nolan, S. P. J. Am. Chem. Soc. 2004, 126, 5046.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 5046
- Lebel, H.¹ Janes, M.K.² Charette, A.B.³ Nolan, S.P.⁴

38
- 18844443420
- Campeau, L.-C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857.
- (2005) Org. Lett , vol.7 , pp. 1857
- Campeau, L.-C.¹ Thansandote, P.² Fagnou, K.³

39
- 45749092491
- Preparation of 4-Phenyl-1,2-dihydronaphthalene (2a) and (1-Phenylbuta-1,3-dienyl)benzene (3a, Typical Procedure Under an N 2 atmosphere, a mixture of 1a (206 mg, 1 mmol, Cl 2PdL2 (20 mg, 0.02 mmol, IMeṡHCl (35 mg, 0.08 mmol) and DMA (2 mL) was stirred for 12 h at 160°C. The reaction was monitored by TLC (eluent: hexane, After the reaction was judged complete, the reaction mixture was allowed to cool. The crude mixture was then loaded directly onto SiO2 and purified by column chromatography using hexane as the eluent to give the products 2a (86 mg, 42, and 3a (14 mg, 7, Compound 2a: colorless oil. IR (film, νmax, 3059, 3026, 2934, 1720, 1662, 1597, 1489, 1447, 1269, 1157 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.49-7.09 (m, 5 H, 7.00 (d, J, 7.4 Hz, 1 H, 6.08 (t, J, 4.7 Hz, 1 H, 2.84 (t, J, 8.1 Hz, 2 H, 2.42-2.37 m
- 3): δ = 143.1, 142.1, 139.6, 134.9, 130.4, 128.5, 128.2. 128.1, 127.6, 127.5, 127.4, 118.6.

40
- 45749144238
- The crystal data of 2f have been deposited at the CCDC with number 671565. Crystal data for 2f: C22H26O2, MW, 322.43, monoclinic, space group P2(1)/c, final R indices [I > 2σ(I, R1, 0.0505, wR2, 0.1033, a, 14.8134(19) Å, b, 16.2215(19) Å, c, 7.7787(10) Å, α, 90°, β, 100.708(2)°, γ, 90°, V, 1836.6(4) Å3, crystal size: 0.482 x 0.435 x 0.276 mm, T, 293 (2) K, Z, 4, reflections collected/unique: 10650/ 3977 Rint, 0.0921, data: 3977, restraints: 0, parameters: 222
- int = 0.0921), data: 3977, restraints: 0, parameters: 222.

41
- 4143123249
- (a) Patil, N. T.; Kadota, I.; Shibuya, A.; Gyoung, Y. S.; Yamamoto, Y. Adv. Synth. Catal. 2004, 346, 800.
- (2004) Adv. Synth. Catal , vol.346 , pp. 800
- Patil, N.T.¹ Kadota, I.² Shibuya, A.³ Gyoung, Y.S.⁴ Yamamoto, Y.⁵

42
- 0031742384
- (b) Trost, B. M. Chem. Eur. J. 1998, 4, 2405.
- (1998) Chem. Eur. J , vol.4 , pp. 2405
- Trost, B.M.¹

43
- 0002524474
- (c) Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
- (1990) Acc. Chem. Res , vol.23 , pp. 34
- Trost, B.M.¹

44
- 0001342781
- (d) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161.
- (1987) J. Am. Chem. Soc , vol.109 , pp. 3161
- Trost, B.M.¹ Rise, F.²

45
- 0001467798
- For a recent review on hydrido complexes of palladium, see
- For a recent review on hydrido complexes of palladium, see: Grushin, V. V. Chem. Rev. 1996, 96, 2011.
- (1996) Chem. Rev , vol.96 , pp. 2011
- Grushin, V.V.¹

46
- 0036800380
- For reviews on C-H activation, see: a
- For reviews on C-H activation, see: (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
- (2002) Acc. Chem. Res , vol.35 , pp. 826
- Kakiuchi, F.¹ Murai, S.²

47
- 0035984037
- (b) Li, C.-J. Acc. Chem. Res. 2002, 35, 533.
- (2002) Acc. Chem. Res , vol.35 , pp. 533
- Li, C.-J.¹

48
- 0036589261
- (c)Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
- (2002) Chem. Rev , vol.102 , pp. 1731
- Ritleng, V.¹ Sirlin, C.² Pfeffer, M.³

49
- 0742313935
- (d) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 212.
- (2002) Top. Curr. Chem , vol.219 , pp. 212
- Miura, M.¹ Nomura, M.²

50
- 0033553817
- (e) Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1698
- Dyker, G.¹

51
- 0012233552
- (f) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
- (1997) Chem. Rev , vol.97 , pp. 2879
- Shilov, A.E.¹ Shul'pin, G.B.²

52
- 0348134916
- For related intramolecular alkyl-aryl coupling reactions, see: a
- For related intramolecular alkyl-aryl coupling reactions, see: (a) Baudoin, O.; Herrbach, A.; Guéritte, F. Angew. Chem. Int. Ed. 2003, 42, 5736.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 5736
- Baudoin, O.¹ Herrbach, A.² Guéritte, F.³

53
- 0010821235
- (b) Dyker, G. Chem. Ber. 1994, 127, 739.
- (1994) Chem. Ber , vol.127 , pp. 739
- Dyker, G.¹

54
- 0001468409
- (c) Dyker, G. J. Org. Chem. 1993, 58, 6426.
- (1993) J. Org. Chem , vol.58 , pp. 6426
- Dyker, G.¹

55
- 33748243464
- (d) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023.
- (1992) Angew. Chem., Int. Ed. Engl , vol.31 , pp. 1023
- Dyker, G.¹

56
- 34347214018
- (a) Lu, J.; Tan, X.; Chen, C. J. Am. Chem. Soc. 2007, 129, 7768.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 7768
- Lu, J.¹ Tan, X.² Chen, C.³

57
- 0141923586
- (b) Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 12084
- Hennessy, E.J.¹ Buchwald, S.L.²

58
- 0037936773
- (c) Sezen, B.; Sames, D. J. Am. Chem. Soc. 2003, 125, 5274.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5274
- Sezen, B.¹ Sames, D.²

59
- 0037562071
- (d) Glover, B.; Harvey, K. A.; Liu, B.; Sharp, M. J.; Tymoschenko, M. F. Org. Lett. 2003, 5, 301.
- (2003) Org. Lett , vol.5 , pp. 301
- Glover, B.¹ Harvey, K.A.² Liu, B.³ Sharp, M.J.⁴ Tymoschenko, M.F.⁵

60
- 0037771626
- (e) Toyota, M.; Ilangovan, A.; Okamoto, R.; Masaki, T.; Arakawa, M.; Ihara, M. Org. Lett. 2002, 4, 4293.
- (2002) Org. Lett , vol.4 , pp. 4293
- Toyota, M.¹ Ilangovan, A.² Okamoto, R.³ Masaki, T.⁴ Arakawa, M.⁵ Ihara, M.⁶

61
- 0037012743
- (f) Hughes, C. C.; Trauner, D. Angew. Chem. Int. Ed. 2002, 41, 1569.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1569
- Hughes, C.C.¹ Trauner, D.²

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