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Volumn 71, Issue 49, 2015, Pages 9245-9250

Pd-catalyzed decarboxylative coupling of arylalkynyl carboxylic acids with allyl ethers: Regioselective synthesis of branched 1,3-enynes

(3) Jiao, Jun Ying a Zhang, Xing Guo a Zhang, Xiao Hong a

a WENZHOU UNIVERSITY (China)

Author keywords

1,3 enyne; Allylic ether; Arylalkynyl carboxylic acid; Decarboxylative coupling

Indexed keywords

ALLYL COMPOUND; CARBOXYLIC ACID; ETHER DERIVATIVE; PALLADIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; COMPARATIVE STUDY; CONTROLLED STUDY; DECARBOXYLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REGIOSELECTIVELY; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 84947558953 PISSN: 00404020 EISSN: 14645416 Source Type: Journal
DOI: 10.1016/j.tet.2015.10.036 Document Type: Article

Times cited : (10)

References (65)

1
- 58149154535
- H.M. Sheldrake, G. Jamieson, S.I. Pascu, and J.W. Burton Org. Biomol. Chem. 7 2009 238
- (2009) Org. Biomol. Chem. , vol.7 , pp. 238
- Sheldrake, H.M.¹ Jamieson, G.² Pascu, S.I.³ Burton, J.W.⁴

2
- 30344442147
- J.H. Chen, L. Ying, T.M. Hansen, M.M. Engler, C.S. Lee, J.J.L. Clari, and C.J. Forsyth Bioorg. Med. Chem. Lett. 16 2006 901
- (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 901
- Chen, J.H.¹ Ying, L.² Hansen, T.M.³ Engler, M.M.⁴ Lee, C.S.⁵ Clari, J.J.L.⁶ Forsyth, C.J.⁷

3
- 0038527227
- N. El-Jaber, A. Estevez-Braun, A.G. Ravelo, O. Munoz-Munoz, A. Rodriguez-Afonso, and J.R. Murguia J. Nat. Prod. 66 2003 722
- (2003) J. Nat. Prod. , vol.66 , pp. 722
- El-Jaber, N.¹ Estevez-Braun, A.² Ravelo, A.G.³ Munoz-Munoz, O.⁴ Rodriguez-Afonso, A.⁵ Murguia, J.R.⁶

4
- 0035140106
- A. Fontana, G. d'Ippolito, L. D'Souza, E. Mollo, P.S. Parameswaram, and G. Cimino J. Nat. Prod. 64 2001 131
- (2001) J. Nat. Prod. , vol.64 , pp. 131
- Fontana, A.¹ D'Ippolito, G.² D'Souza, L.³ Mollo, E.⁴ Parameswaram, P.S.⁵ Cimino, G.⁶

5
- 0030059382
- M. Alami, F. Ferri, and Y. Gasiain Tetrahedron Lett. 37 1996 57
- (1996) Tetrahedron Lett. , vol.37 , pp. 57
- Alami, M.¹ Ferri, F.² Gasiain, Y.³

6
- 0035107812
- S.L. Iverson, and J.P. Uetrecht Chem. Res. Toxicol. 14 2001 175
- (2001) Chem. Res. Toxicol. , vol.14 , pp. 175
- Iverson, S.L.¹ Uetrecht, J.P.²

7
- 84863614096
- X.R. Song, X.F. Xia, Q.B. Song, F. Yang, Y.X. Li, X.Y. Liu, and Y.M. Liang Org. Lett. 14 2012 3344
- (2012) Org. Lett. , vol.14 , pp. 3344
- Song, X.R.¹ Xia, X.F.² Song, Q.B.³ Yang, F.⁴ Li, Y.X.⁵ Liu, X.Y.⁶ Liang, Y.M.⁷

8
- 33745527079
- J.J. Xu, and D.J. Burton Org. Lett. 8 2006 2555
- (2006) Org. Lett. , vol.8 , pp. 2555
- Xu, J.J.¹ Burton, D.J.²

9
- 84947545623
- V. Gracias, A.F. Gasiecki, and S.W. Djuric Tetrahedron Lett. 46 2005 9409
- (2005) Tetrahedron Lett. , vol.46 , pp. 9409
- Gracias, V.¹ Gasiecki, A.F.² Djuric, S.W.³

10
- 80051712408
- J.L. Chen, F. Zheng, Y.G. Huang, and F.L. Qing J. Org. Chem. 76 2011 6525
- (2011) J. Org. Chem. , vol.76 , pp. 6525
- Chen, J.L.¹ Zheng, F.² Huang, Y.G.³ Qing, F.L.⁴

11
- 84055200429
- Y.S. Chun, J.H. Lee, J.H. Kim, Y.O. Ko, and S.-G. Lee Org. Lett. 13 2011 6390
- (2011) Org. Lett. , vol.13 , pp. 6390
- Chun, Y.S.¹ Lee, J.H.² Kim, J.H.³ Ko, Y.O.⁴ Lee, S.-G.⁵

12
- 0001326010
- G. Zweifel, and N.L. Polston J. Am. Chem. Soc. 92 1970 4068
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 4068
- Zweifel, G.¹ Polston, N.L.²

13
- 0031592594
- J.F. Betzer, J. Ardisson, J. Yves, and A. Pancrazi Tetrahedron Lett. 38 1997 2279
- (1997) Tetrahedron Lett. , vol.38 , pp. 2279
- Betzer, J.F.¹ Ardisson, J.² Yves, J.³ Pancrazi, A.⁴

14
- 84892893160
- X. Li, F. Peng, M. Zhou, M. Mo, R. Zhao, and Z. Shao Chem. Commun. 2014 1745
- (2014) Chem. Commun. , pp. 1745
- Li, X.¹ Peng, F.² Zhou, M.³ Mo, M.⁴ Zhao, R.⁵ Shao, Z.⁶

15
- 0034665126
- R. Mahrwald, and S. Quint Tetrahedron 56 2000 7463
- (2000) Tetrahedron , vol.56 , pp. 7463
- Mahrwald, R.¹ Quint, S.²

16
- 63349110873
- V. Hadi, K.S. Yoo, M. Jeong, and K.W. Jung Tetrahedron Lett. 50 2009 2370
- (2009) Tetrahedron Lett. , vol.50 , pp. 2370
- Hadi, V.¹ Yoo, K.S.² Jeong, M.³ Jung, K.W.⁴

17
- 79957992135
- B.M. Trost, B.R. Taft, J. Masters, and J.-P. Lumb J. Am. Chem. Soc. 133 2011 8502
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 8502
- Trost, B.M.¹ Taft, B.R.² Masters, J.³ Lumb, J.-P.⁴

18
- 2442497335
- C.G. Bates, P. Saejueng, and D. Venkataraman Org. Lett. 6 2004 1441
- (2004) Org. Lett. , vol.6 , pp. 1441
- Bates, C.G.¹ Saejueng, P.² Venkataraman, D.³

19
- 84867691338
- Y.X. Zhang, Z.J. Li, and Z.Q. Liu Org. Lett. 14 2012 1226
- (2012) Org. Lett. , vol.14 , pp. 1226
- Zhang, Y.X.¹ Li, Z.J.² Liu, Z.Q.³

20
- 33751405154
- J. Boukouvalas, S. Côté, and B. Ndzi Tetrahedron Lett. 48 2007 105
- (2007) Tetrahedron Lett. , vol.48 , pp. 105
- Boukouvalas, J.¹ Côté, S.² Ndzi, B.³

21
- 28444445923
- M. Feuerstein, L. Chahen, H. Doucet, and M. Santelli Tetrahedron 62 2006 112
- (2006) Tetrahedron , vol.62 , pp. 112
- Feuerstein, M.¹ Chahen, L.² Doucet, H.³ Santelli, M.⁴

22
- 82255164730
- M.M. Huang, Y.J. Feng, and Y.J. Wu Tetrahedron 68 2012 376
- (2012) Tetrahedron , vol.68 , pp. 376
- Huang, M.M.¹ Feng, Y.J.² Wu, Y.J.³

23
- 1242293079
- M. Pal, K. Parasuraman, V. Subramanian, R. Dakarapu, and K.R. Yeleswarapu Tetrahedron Lett. 45 2004 2305
- (2004) Tetrahedron Lett. , vol.45 , pp. 2305
- Pal, M.¹ Parasuraman, K.² Subramanian, V.³ Dakarapu, R.⁴ Yeleswarapu, K.R.⁵

24
- 0000459210
- M. Alami, B. Crousse, and F. Ferri J. Organomet.Chem. 624 2001 114
- (2001) J. Organomet.Chem. , vol.624 , pp. 114
- Alami, M.¹ Crousse, B.² Ferri, F.³

25
- 84860371797
- A. Souffrin, C. Croix, M. Claude, and V. Massuard Eur. J. Org. Chem. 2012 2499
- (2012) Eur. J. Org. Chem. , pp. 2499
- Souffrin, A.¹ Croix, C.² Claude, M.³ Massuard, V.⁴

26
- 84947606826
- D. Alevs, J.S.D. Reis, C. Luchese, C.W. Nogueira, and G. Zeni Eur. J. Org. Chem. 2008 377
- (2008) Eur. J. Org. Chem. , pp. 377
- Alevs, D.¹ Reis, J.S.D.² Luchese, C.³ Nogueira, C.W.⁴ Zeni, G.⁵

27
- 27144472813
- J.H. Li, X.D. Zhang, and Y.X. Xie Eur. J. Org. Chem. 2005 4256
- (2005) Eur. J. Org. Chem. , pp. 4256
- Li, J.H.¹ Zhang, X.D.² Xie, Y.X.³

28
- 0344835674
- Z. Novak, A. Szabo, J. Repasi, and A. Kotschy J. Org. Chem. 68 2003 3327
- (2003) J. Org. Chem. , vol.68 , pp. 3327
- Novak, Z.¹ Szabo, A.² Repasi, J.³ Kotschy, A.⁴

29
- 53849142185
- M.Y. Wu, J.C. Mao, J. Guo, and S.J. Ji Eur. J. Org. Chem. 2008 4050
- (2008) Eur. J. Org. Chem. , pp. 4050
- Wu, M.Y.¹ Mao, J.C.² Guo, J.³ Ji, S.J.⁴

30
- 22244450348
- P. Saejueng, C.G. Bates, and D. Venkataraman Synthesis 10 2005 1706
- (2005) Synthesis , vol.10 , pp. 1706
- Saejueng, P.¹ Bates, C.G.² Venkataraman, D.³

31
- 84880136818
- P. Sun, H. Yan, L. Lu, D. Liu, G. Rong, and J. Mao Tetrahedron 69 2013 6969
- (2013) Tetrahedron , vol.69 , pp. 6969
- Sun, P.¹ Yan, H.² Lu, L.³ Liu, D.⁴ Rong, G.⁵ Mao, J.⁶

32
- 67549144799
- X. Xie, X.B. Xu, H.F. Li, X.L. Xu, J.Y. Yang, and Y.Z. Li Adv. Synth. Catal. 351 2009 1263
- (2009) Adv. Synth. Catal. , vol.351 , pp. 1263
- Xie, X.¹ Xu, X.B.² Li, H.F.³ Xu, X.L.⁴ Yang, J.Y.⁵ Li, Y.Z.⁶

33
- 60849111849
- T. Hatakeyama, Y. Yoshimoto, T. Gabriel, and M. Nakamura Org. Lett. 10 2008 5341
- (2008) Org. Lett. , vol.10 , pp. 5341
- Hatakeyama, T.¹ Yoshimoto, Y.² Gabriel, T.³ Nakamura, M.⁴

34
- 2442522583
- Y. Masuda, M. Murata, K. Sato, and S. Watanabe Chem. Commun. 1998 807 For alkynylmagnesium, see
- (1998) Chem. Commun. , pp. 807
- Masuda, Y.¹ Murata, M.² Sato, K.³ Watanabe, S.⁴

35
- 0001424603
- H.P. Dang, and G. Linstrumelle Tetrahedron Lett. 1978 191 For alkynyl-silicon, see
- (1978) Tetrahedron Lett. , pp. 191
- Dang, H.P.¹ Linstrumelle, G.²

36
- 0035856930
- J.A. Marshall, H.R. Chobanian, and M.M. Yanik Org. Lett. 3 2001 4107
- (2001) Org. Lett. , vol.3 , pp. 4107
- Marshall, J.A.¹ Chobanian, H.R.² Yanik, M.M.³

37
- 0142248461
- T.P. Heffron, J.D. Trenkle, and T.F. Jamison Tetrahedron 59 2003 8913 For alkynyltin, see
- (2003) Tetrahedron , vol.59 , pp. 8913
- Heffron, T.P.¹ Trenkle, J.D.² Jamison, T.F.³

38
- 33845281119
- J.K. Stille, and B.L. Groh J. Am. Chem. Soc. 109 1987 813
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 813
- Stille, J.K.¹ Groh, B.L.²

39
- 2342592732
- L.R. Pottier, J.F. Peyrat, M. Alami, and J.D. Brion Tetrahedron Lett. 45 2004 4035
- (2004) Tetrahedron Lett. , vol.45 , pp. 4035
- Pottier, L.R.¹ Peyrat, J.F.² Alami, M.³ Brion, J.D.⁴

40
- 0001761892
- J.K. Stille, and J.H. Simpson J. Am. Chem. Soc. 109 1987 2138 For alkynylzinc, see
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2138
- Stille, J.K.¹ Simpson, J.H.²

41
- 0041728814
- E.I. Negishi, M.X. Qian, F.X. Zeng, L. Anastasia, and D. Babinski Org. Lett. 5 2003 1597
- (2003) Org. Lett. , vol.5 , pp. 1597
- Negishi, E.I.¹ Qian, M.X.² Zeng, F.X.³ Anastasia, L.⁴ Babinski, D.⁵

42
- 33947094318
- E. Negishi, N. Okukado, A.O. King, D.E. Vanhorn, and B.I. Spiegel J. Am. Chem. Soc. 100 1978 2254 For alkenylboranes, see
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 2254
- Negishi, E.¹ Okukado, N.² King, A.O.³ Vanhorn, D.E.⁴ Spiegel, B.I.⁵

43
- 0000220284
- H. Lipshutz, and S. Sengupta Org. React. 41 1992 135 For alkenylcopper, see
- (1992) Org. React. , vol.41 , pp. 135
- Lipshutz, H.¹ Sengupta, S.²

44
- 84947608401
- I. Nobuo, A. Isao, and Y. Hisashi J. Am. Chem. Soc. 108 1986 3
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 3
- Nobuo, I.¹ Isao, A.² Hisashi, Y.³

45
- 0040433921
- Z. Marek, R.B. Jacek, and S.L. Wojciech J. Organomet. Chem. 580 1999 354 For alkenylmagnesium, see
- (1999) J. Organomet. Chem. , vol.580 , pp. 354
- Marek, Z.¹ Jacek, R.B.² Wojciech, S.L.³

46
- 84947593974
- N. Tomihiro, S. Takeshi, S. Hiroshi, A. Kazushige, K. Hideaki, and K. Kenichi Chem. Lett. 25 1996 549
- (1996) Chem. Lett. , vol.25 , pp. 549
- Tomihiro, N.¹ Takeshi, S.² Hiroshi, S.³ Kazushige, A.⁴ Hideaki, K.⁵ Kenichi, K.⁶

47
- 79953167852
- J. Park, E. Park, A. Kim, S.A. Park, Y. Lee, K.W. Chi, Y.H. Jung, and I.S. Kim J. Org. Chem. 76 2011 2214
- (2011) J. Org. Chem. , vol.76 , pp. 2214
- Park, J.¹ Park, E.² Kim, A.³ Park, S.A.⁴ Lee, Y.⁵ Chi, K.W.⁶ Jung, Y.H.⁷ Kim, I.S.⁸

48
- 64549098217
- J. Moon, M. Jang, and S. Lee J. Org. Chem. 74 2009 1403
- (2009) J. Org. Chem. , vol.74 , pp. 1403
- Moon, J.¹ Jang, M.² Lee, S.³

49
- 77955142798
- W.W. Zhang, X.G. Zhang, and J.H. Li J. Org. Chem. 75 2010 5259
- (2010) J. Org. Chem. , vol.75 , pp. 5259
- Zhang, W.W.¹ Zhang, X.G.² Li, J.H.³

50
- 43549101428
- J. Moon, M. Jeong, H. Nam, J.H. Ju, J.H. Moon, H.M. Jung, and S. Lee Org. Lett. 10 2008 945
- (2008) Org. Lett. , vol.10 , pp. 945
- Moon, J.¹ Jeong, M.² Nam, H.³ Ju, J.H.⁴ Moon, J.H.⁵ Jung, H.M.⁶ Lee, S.⁷

51
- 84898060263
- J. Hwang, K. Park, J. Choe, H. Min, K.H. Song, and S. Lee J. Org. Chem. 79 2014 3267
- (2014) J. Org. Chem. , vol.79 , pp. 3267
- Hwang, J.¹ Park, K.² Choe, J.³ Min, H.⁴ Song, K.H.⁵ Lee, S.⁶

52
- 84934982660
- W.-X. Lv, Y.-F. Zeng, S.-S. Zhang, Q. Li, and H. Wang Org. Lett. 17 2015 2972
- (2015) Org. Lett. , vol.17 , pp. 2972
- Lv, W.-X.¹ Zeng, Y.-F.² Zhang, S.-S.³ Li, Q.⁴ Wang, H.⁵

53
- 84877124826
- X. Li, F. Yang, and Y. Wu J. Org. Chem. 78 2013 4543
- (2013) J. Org. Chem. , vol.78 , pp. 4543
- Li, X.¹ Yang, F.² Wu, Y.³

54
- 84879998213
- K. Park, Y. Heo, and S. Lee Org. Lett. 15 2013 3322
- (2013) Org. Lett. , vol.15 , pp. 3322
- Park, K.¹ Heo, Y.² Lee, S.³

55
- 84906082063
- J. Lim, K. Park, A. Byeun, and S. Lee Tetrahedron Lett. 55 2014 4875
- (2014) Tetrahedron Lett. , vol.55 , pp. 4875
- Lim, J.¹ Park, K.² Byeun, A.³ Lee, S.⁴

56
- 84890893209
- D.L. Priebbenow, P. Becker, and C. Bolm Org. Lett. 15 2013 6155
- (2013) Org. Lett. , vol.15 , pp. 6155
- Priebbenow, D.L.¹ Becker, P.² Bolm, C.³

57
- 84909986838
- G. Hu, Y. Gao, and Y. Zhao Org. Lett. 16 2014 4464
- (2014) Org. Lett. , vol.16 , pp. 4464
- Hu, G.¹ Gao, Y.² Zhao, Y.³

58
- 84926456212
- M. Zhou, M. Chen, Y. Zhou, K. Yang, J. Su, J. Du, and Q. Song Org. Lett. 17 2015 1786
- (2015) Org. Lett. , vol.17 , pp. 1786
- Zhou, M.¹ Chen, M.² Zhou, Y.³ Yang, K.⁴ Su, J.⁵ Du, J.⁶ Song, Q.⁷

59
- 84893852848
- X. Li, F. Yang, Y. Wu, and Y. Wu Org. Lett. 16 2014 992
- (2014) Org. Lett. , vol.16 , pp. 992
- Li, X.¹ Yang, F.² Wu, Y.³ Wu, Y.⁴

60
- 84870003448
- N.J. Rijs, and R.A.J. O'Hair Organometallics 31 2012 8012
- (2012) Organometallics , vol.31 , pp. 8012
- Rijs, N.J.¹ O'Hair, R.A.J.²

61
- 84867878192
- A. Pyo, Y.H. Kim, K. Park, G.C. Kim, H.C. Choi, and S. Lee Appl. Organometal. Chem. 26 2012 650
- (2012) Appl. Organometal. Chem. , vol.26 , pp. 650
- Pyo, A.¹ Kim, Y.H.² Park, K.³ Kim, G.C.⁴ Choi, H.C.⁵ Lee, S.⁶

62
- 84867731594
- Org. Lett. 2014, 16, 3611
- Y.L. Shao, X.H. Zhang, J.S. Han, and P. Zhong Org. Lett. 14 2012 5242 Org. Lett. 2014, 16, 3611
- (2012) Org. Lett. , vol.14 , pp. 5242
- Shao, Y.L.¹ Zhang, X.H.² Han, J.S.³ Zhong, P.⁴

63
- 0037174448
- A.G. Myers, D. Tanaka, and M.R.J. Mannion Am. Chem. Soc. 124 2002 11250
- (2002) Am. Chem. Soc. , vol.124 , pp. 11250
- Myers, A.G.¹ Tanaka, D.² Mannion, M.R.J.³

64
- 84862908263
- Y.X. Zhang, Z.J. Li, and Z.Q. Liu Org. Lett. 14 2012 226
- (2012) Org. Lett. , vol.14 , pp. 226
- Zhang, Y.X.¹ Li, Z.J.² Liu, Z.Q.³

65
- 48849110621
- D.L. Pan, A.J. Chen, Y.J. Su, W. Zhou, S. Li, W. Jia, J. Xiao, Q.J. Liu, L.G. Zhang, and N. Jiao Angew. Chem. Int. Ed. 47 2008 4729
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4729
- Pan, D.L.¹ Chen, A.J.² Su, Y.J.³ Zhou, W.⁴ Li, S.⁵ Jia, W.⁶ Xiao, J.⁷ Liu, Q.J.⁸ Zhang, L.G.⁹ Jiao, N.¹⁰

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