SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 23, 2014, Pages 5931-5935

On-line reaction monitoring and mechanistic studies by mass spectrometry: Negishi cross-coupling, hydrogenolysis, and reductive amination

(6) Yan, Xin a Sokol, Ewa a Li, Xin a Li, Guangtao a Xu, Shiqing a Cooks, R Graham a

a PURDUE UNIVERSITY (United States)

Author keywords

air moisture sensitive reactions; cross coupling; mass spectrometry; reaction intermediates; reaction kinetics

Indexed keywords

CATALYSIS; HYDROGENOLYSIS; HYDROLYSIS; MASS SPECTROMETRY; MOISTURE; REACTION KINETICS;

CONCENTRATED SOLUTION; CROSS-COUPLINGS; ESI MASS SPECTROMETRY; HETEROGENEOUS REACTIONS; MECHANISTIC STUDIES; NEGISHI CROSS-COUPLING; ORGANIC REACTION MECHANISMS; REDUCTIVE AMINATION;

REACTION INTERMEDIATES;

PALLADIUM;

AMINATION; CATALYSIS; CHEMISTRY; MASS SPECTROMETRY;

AMINATION; CATALYSIS; MASS SPECTROMETRY; PALLADIUM;

EID: 84901705779 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201310493 Document Type: Article

Times cited : (82)

References (52)

1
- 84961977057
- G. W. Amarante, M. Benassi, H. M. S. Milagre, A. A. C. Braga, F. Maseras, M. N. Eberlin, F. Coelho, Chem. Eur. J. 2009, 15, 12460-12469
- (2009) Chem. Eur. J. , vol.15 , pp. 12460-12469
- Amarante, G.W.¹ Benassi, M.² Milagre, H.M.S.³ Braga, A.A.C.⁴ Maseras, F.⁵ Eberlin, M.N.⁶ Coelho, F.⁷

2
- 0034716179
- N. M. M. Nibbering, Int. J. Mass Spectrom. 2000, 200, 27-42
- (2000) Int. J. Mass Spectrom. , vol.200 , pp. 27-42
- Nibbering, N.M.M.¹

3
- 0037425570
- M. Vairamani, M. L. Gross, J. Am. Chem. Soc. 2003, 125, 42-43
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 42-43
- Vairamani, M.¹ Gross, M.L.²

4
- 26844485585
- L. S. Santos, L. Knaack, J. O. Metzger, Int. J. Mass Spectrom. 2005, 246, 84-104
- (2005) Int. J. Mass Spectrom. , vol.246 , pp. 84-104
- Santos, L.S.¹ Knaack, L.² Metzger, J.O.³

5
- 84893319864
- L. P. E. Yunker, R. L. Stoddard, J. S. McIndoe, J. Mass Spectrom. 2014, 49, 1-8
- (2014) J. Mass Spectrom. , vol.49 , pp. 1-8
- Yunker, L.P.E.¹ Stoddard, R.L.² McIndoe, J.S.³

6
- 84878223516
- K. Chung, S. M. Banik, A. G. De Crisci, D. M. Pearson, T. R. Blake, J. V. Olsson, A. J. Ingram, R. N. Zare, R. M. Waymouth, J. Am. Chem. Soc. 2013, 135, 7593-7602
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 7593-7602
- Chung, K.¹ Banik, S.M.² De Crisci, A.G.³ Pearson, D.M.⁴ Blake, T.R.⁵ Olsson, J.V.⁶ Ingram, A.J.⁷ Zare, R.N.⁸ Waymouth, R.M.⁹

7
- 84868598685
- R. H. Perry, T. J. Cahill, J. L. Roizen, J. Du Bois, R. N. Zare, Proc. Natl. Acad. Sci. USA 2012, 109, 18295-18299
- (2012) Proc. Natl. Acad. Sci. USA , vol.109 , pp. 18295-18299
- Perry, R.H.¹ Cahill, T.J.² Roizen, J.L.³ Du Bois, J.⁴ Zare, R.N.⁵

8
- 84857136655
- R. H. Perry, K. R. Brownell, K. Chingin, T. J. Cahill, R. M. Waymouth, R. N. Zare, Proc. Natl. Acad. Sci. USA 2012, 109, 2246-2250
- (2012) Proc. Natl. Acad. Sci. USA , vol.109 , pp. 2246-2250
- Perry, R.H.¹ Brownell, K.R.² Chingin, K.³ Cahill, T.J.⁴ Waymouth, R.M.⁵ Zare, R.N.⁶

9
- 79952273084
- R. H. Perry, M. Splendore, A. Chien, N. K. Davis, R. N. Zare, Angew. Chem. 2011, 123, 264-268
- (2011) Angew. Chem. , vol.123 , pp. 264-268
- Perry, R.H.¹ Splendore, M.² Chien, A.³ Davis, N.K.⁴ Zare, R.N.⁵

10
- 78650713170
- Angew. Chem. Int. Ed. 2011, 50, 250-254
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 250-254

11
- 84870550323
- P. S. D. Robinson, T.-L. Nguyen, H. Lioe, R. A. J. O'Hair, G. N. Khairallah, Int. J. Mass Spectrom. 2012, 330-332, 109-117
- (2012) Int. J. Mass Spectrom. , vol.330-332 , pp. 109-117
- Robinson, P.S.D.¹ Nguyen, T.-L.² Lioe, H.³ O'Hair, R.A.J.⁴ Khairallah, G.N.⁵

12
- 73649124234
- W. Schrader, P. P. Handayani, J. Zhou, B. List, Angew. Chem. 2009, 121, 1491-1494
- (2009) Angew. Chem. , vol.121 , pp. 1491-1494
- Schrader, W.¹ Handayani, P.P.² Zhou, J.³ List, B.⁴

13
- 60149092311
- Angew. Chem. Int. Ed. 2009, 48, 1463-1466
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1463-1466

14
- 53549124798
- C. A. Müller, A. Pfaltz, Angew. Chem. 2008, 120, 3411-3414
- (2008) Angew. Chem. , vol.120 , pp. 3411-3414
- Müller, C.A.¹ Pfaltz, A.²

15
- 53549099942
- for more references, see the Supporting Information.
- Angew. Chem. Int. Ed. 2008, 47, 3363-3366; for more references, see the Supporting Information.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 3363-3366

16
- 79952362055
- F. Marchetti, G. Pampaloni, C. Pinzino, J. Organomet. Chem. 2011, 696, 1294-1300
- (2011) J. Organomet. Chem. , vol.696 , pp. 1294-1300
- Marchetti, F.¹ Pampaloni, G.² Pinzino, C.³

17
- 68149084769
- L. A. Chen, K. Sung, Org. Lett. 2009, 11, 3370-3373
- (2009) Org. Lett. , vol.11 , pp. 3370-3373
- Chen, L.A.¹ Sung, K.²

18
- 0030662180
- C. Felby, B. R. Nielsen, P. O. Skibsted, Appl. Microbiol. Biotechnol. 1997, 48, 459-464
- (1997) Appl. Microbiol. Biotechnol. , vol.48 , pp. 459-464
- Felby, C.¹ Nielsen, B.R.² Skibsted, P.O.³

19
- 28144438821
- O. B. Morozova, S. E. Korchak, R. Z. Sadeev, A. V. Yurkovskaya, J. Phys. Chem. A 2005, 109, 10459-10466.
- (2005) J. Phys. Chem. A , vol.109 , pp. 10459-10466
- Morozova, O.B.¹ Korchak, S.E.² Sadeev, R.Z.³ Yurkovskaya, A.V.⁴

20
- 0022636755
- K. Eckart, H. Schwarz, G. Becker, H. Kessler, J. Org. Chem. 1986, 51, 483-486
- (1986) J. Org. Chem. , vol.51 , pp. 483-486
- Eckart, K.¹ Schwarz, H.² Becker, G.³ Kessler, H.⁴

21
- 0033759908
- J. Lu, R. Zenobi, Fresenius J. Anal. Chem. 2000, 366, 3-9
- (2000) Fresenius J. Anal. Chem. , vol.366 , pp. 3-9
- Lu, J.¹ Zenobi, R.²

22
- 0030764736
- M. R. Carrasco, M. C. Fitzgerald, Y. Oda, S. B. H. Kent, Tetrahedron Lett. 1997, 38, 6331-6334
- (1997) Tetrahedron Lett. , vol.38 , pp. 6331-6334
- Carrasco, M.R.¹ Fitzgerald, M.C.² Oda, Y.³ Kent, S.B.H.⁴

23
- 54349095835
- C. Y. Cheng, C. H. Yuan, S. C. Cheng, M. Z. Huang, H. C. Chang, T. L. Cheng, C. S. Yeh, J. Shiea, Anal. Chem. 2008, 80, 7699-7705
- (2008) Anal. Chem. , vol.80 , pp. 7699-7705
- Cheng, C.Y.¹ Yuan, C.H.² Cheng, S.C.³ Huang, M.Z.⁴ Chang, H.C.⁵ Cheng, T.L.⁶ Yeh, C.S.⁷ Shiea, J.⁸

24
- 70349758443
- Y. Xie, L.-F. He, S.-C. Lin, H.-F. Su, S.-Y. Xie, R.-B. Huang, L.-S. Zheng, J. Am. Soc. Mass Spectrom. 2009, 20, 2087-2092
- (2009) J. Am. Soc. Mass Spectrom. , vol.20 , pp. 2087-2092
- Xie, Y.¹ He, L.-F.² Lin, S.-C.³ Su, H.-F.⁴ Xie, S.-Y.⁵ Huang, R.-B.⁶ Zheng, L.-S.⁷

25
- 34447324692
- C. Petucci, J. Diffendal, D. Kaufman, B. Mekonnen, G. Terefenko, B. Musselman, Anal. Chem. 2007, 79, 5064-5070
- (2007) Anal. Chem. , vol.79 , pp. 5064-5070
- Petucci, C.¹ Diffendal, J.² Kaufman, D.³ Mekonnen, B.⁴ Terefenko, G.⁵ Musselman, B.⁶

26
- 79953190815
- E. L. Harry, A. W. T. Bristow, I. D. Wilson, C. S. Creaser, Analyst 2011, 136, 1728-1732
- (2011) Analyst , vol.136 , pp. 1728-1732
- Harry, E.L.¹ Bristow, A.W.T.² Wilson, I.D.³ Creaser, C.S.⁴

27
- 77952892404
- Z. Yu, L. C. Chen, R. Erra-Balsells, H. Nonami, K. Hiraoka, Rapid Commun. Mass Spectrom. 2010, 24, 1507-1513
- (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 1507-1513
- Yu, Z.¹ Chen, L.C.² Erra-Balsells, R.³ Nonami, H.⁴ Hiraoka, K.⁵

28
- 78049386829
- T. Y. Chen, C. S. Chao, K. K. T. Mong, Y. C. Chen, Chem. Commun. 2010, 46, 8347-8349
- (2010) Chem. Commun. , vol.46 , pp. 8347-8349
- Chen, T.Y.¹ Chao, C.S.² Mong, K.K.T.³ Chen, Y.C.⁴

29
- 78651234120
- A. W. Nørgaard, B. G. Vaz, F. R. Lauritsen, M. N. Eberlin, Rapid Commun. Mass Spectrom. 2010, 24, 3441-3446
- (2010) Rapid Commun. Mass Spectrom. , vol.24 , pp. 3441-3446
- Nørgaard, A.W.¹ Vaz, B.G.² Lauritsen, F.R.³ Eberlin, M.N.⁴

30
- 84868139292
- C. H. Hsieh, C. S. Chao, K. K. T. Mong, Y. C. Chen, J. Mass Spectrom. 2012, 47, 586-590
- (2012) J. Mass Spectrom. , vol.47 , pp. 586-590
- Hsieh, C.H.¹ Chao, C.S.² Mong, K.K.T.³ Chen, Y.C.⁴

31
- 56149085481
- L. Zhu, G. Gamez, H. W. Chen, H. X. Huang, K. Chingin, R. Zenobi, Rapid Commun. Mass Spectrom. 2008, 22, 2993-2998
- (2008) Rapid Commun. Mass Spectrom. , vol.22 , pp. 2993-2998
- Zhu, L.¹ Gamez, G.² Chen, H.W.³ Huang, H.X.⁴ Chingin, K.⁵ Zenobi, R.⁶

32
- 70349313496
- X. Ma, S. Zhang, Z. Lin, Y. Liu, Z. Xing, C. Yang, X. Zhang, Analyst 2009, 134, 1863-1867
- (2009) Analyst , vol.134 , pp. 1863-1867
- Ma, X.¹ Zhang, S.² Lin, Z.³ Liu, Y.⁴ Xing, Z.⁵ Yang, C.⁶ Zhang, X.⁷

33
- 84862781673
- X. Ma, S. Zhang, X. Zhang, TrAC Trends Anal. Chem. 2012, 35, 50-66.
- (2012) TrAC Trends Anal. Chem. , vol.35 , pp. 50-66
- Ma, X.¹ Zhang, S.² Zhang, X.³

34
- 84885449258
- G. Huang, G. Li, R. G. Cooks, Angew. Chem. 2011, 123, 10081-10084
- (2011) Angew. Chem. , vol.123 , pp. 10081-10084
- Huang, G.¹ Li, G.² Cooks, R.G.³

35
- 80053916196
- Angew. Chem. Int. Ed. 2011, 50, 9907-9910
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 9907-9910

36
- 80053920365
- G. Huang, G. Li, J. Ducan, Z. Ouyang, R. G. Cooks, Angew. Chem. 2011, 123, 2551-2554
- (2011) Angew. Chem. , vol.123 , pp. 2551-2554
- Huang, G.¹ Li, G.² Ducan, J.³ Ouyang, Z.⁴ Cooks, R.G.⁵

37
- 79952261474
- Angew. Chem. Int. Ed. 2011, 50, 2503-2506.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2503-2506

38
- 79954458570
- N. Chetwani, C. A. Cassou, D. B. Go, H. C. Chang, Anal. Chem. 2011, 83, 3017-3023.
- (2011) Anal. Chem. , vol.83 , pp. 3017-3023
- Chetwani, N.¹ Cassou, C.A.² Go, D.B.³ Chang, H.C.⁴

39
- 78650907902
- I. Larrosa, C. Somoza, A. Banquy, S. M. Goldup, Org. Lett. 2011, 13, 146-149
- (2011) Org. Lett. , vol.13 , pp. 146-149
- Larrosa, I.¹ Somoza, C.² Banquy, A.³ Goldup, S.M.⁴

40
- 83755162434
- E.-i. Negishi, Angew. Chem. 2011, 123, 6870-6897
- (2011) Angew. Chem. , vol.123 , pp. 6870-6897
- Negishi, E.-I.¹

41
- 79960264489
- Angew. Chem. Int. Ed. 2011, 50, 6738-6764
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 6738-6764

42
- 32344433949
- Elsevier, Amsterdam, .
- L. Kürti, B. Czakõ, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam 2005, pp. 310.
- (2005) Strategic Applications of Named Reactions in Organic Synthesis , pp. 310
- Kürti, L.¹ Czakõ, B.²

43
- 84859756665
- K. L. Vikse, Z. Ahmadi, C. C. Manning, D. A. Harrington, J. S. McIndoe, Angew. Chem. 2011, 123, 8454-8456
- (2011) Angew. Chem. , vol.123 , pp. 8454-8456
- Vikse, K.L.¹ Ahmadi, Z.² Manning, C.C.³ Harrington, D.A.⁴ McIndoe, J.S.⁵

44
- 80052085914
- Angew. Chem. Int. Ed. 2011, 50, 8304-8306.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8304-8306

45
- 84901704320
- T. Müller, A. Badu-Tawiah, R. G. Cooks, Angew. Chem. 2012, 124, 12002-12005
- (2012) Angew. Chem. , vol.124 , pp. 12002-12005
- Müller, T.¹ Badu-Tawiah, A.² Cooks, R.G.³

46
- 84869484006
- Angew. Chem. Int. Ed. 2012, 51, 11832-11835.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11832-11835

47
- 0000868533
- J. Halpern, Science 1982, 217, 401-407.
- (1982) Science , vol.217 , pp. 401-407
- Halpern, J.¹

48
- 34547602950
- L. Xing, X. Wang, C. Cheng, R. Zhu, B. Liu, Y. Hu, Tetrahedron 2007, 63, 9382-9386
- (2007) Tetrahedron , vol.63 , pp. 9382-9386
- Xing, L.¹ Wang, X.² Cheng, C.³ Zhu, R.⁴ Liu, B.⁵ Hu, Y.⁶

49
- 0027181059
- A. Merz, M. Rauschel, Synthesis 1993, 797-802
- (1993) Synthesis , pp. 797-802
- Merz, A.¹ Rauschel, M.²

50
- 3042706907
- K. S. Sagar, C. Chang, W. Wang, J. Lin, S. Lee, Bioorg. Med. Chem. 2004, 12, 4045-4054
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 4045-4054
- Sagar, K.S.¹ Chang, C.² Wang, W.³ Lin, J.⁴ Lee, S.⁵

51
- 0003590063
- Wiley, New York, Chap. 5
- S. Nishimura, Handbook of heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001, Chap. 5
- (2001) Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis
- Nishimura, S.¹

52
- 84901719553
- T. J. Connolly, M. Matchett, P. McGarry, R. T. Swann, J. Med. Chem. 1996, 39, 46-55.
- (1996) J. Med. Chem. , vol.39 , pp. 46-55
- Connolly, T.J.¹ Matchett, M.² McGarry, P.³ Swann, R.T.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.