SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 32, 2014, Pages 8416-8420

Continuous flow synthesis of ketones from carbon dioxide and organolithium or grignard reagents

(6) Wu, Jie a Yang, Xiaoqing b He, Zhi a Mao, Xianwen b Hatton, T Alan b Jamison, Timothy F a

a MASSACHUSETTS INSTITUTE OF TECHNOLOGY (United States)

b Massachusetts Institute of Technology Cambridge (United States)

Author keywords

gas liquid continuous flow; Grignard reactions; ketones; organic lithium reactivity

Indexed keywords

BYPRODUCTS; KETONES; ORGANOMETALLICS;

CONTINUOUS FLOWS; CONTINUOUS-FLOW SYNTHESIS; FLOW PROCESS; GRIGNARD REACTION; GRIGNARD REAGENT; ORGANOLITHIUMS; ORGANOMETALLIC REAGENT; TERTIARY ALCOHOLS;

CARBON DIOXIDE;

EID: 84905365781 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201405014 Document Type: Article

Times cited : (91)

References (70)

1
- 84889336887
- 5ed th ed Wiley-VCH, Weinheim
- H. Surgurg, J. Panten, Common Fragrance and Flavor Materials, 5ed th ed Wiley-VCH, Weinheim, 2006
- (2006) Common Fragrance and Flavor Materials
- Surgurg, H.¹ Panten, J.²

2
- 18944384707
- M. VandePutte, T. Roskams, J. R. Vandenheede, P. Agostinis, P. A. M. deWitte, Br. J. Cancer 2005, 92, 1406
- (2005) Br. J. Cancer , vol.92 , pp. 1406
- Vandeputte, M.¹ Roskams, T.² Vandenheede, J.R.³ Agostinis, P.⁴ Dewitte, P.A.M.⁵

3
- 0023764824
- Y. Nishizuka, Nature 1988, 334, 661
- (1988) Nature , vol.334 , pp. 661
- Nishizuka, Y.¹

4
- 0034143198
- A. M. Prince, D. Pascual, D. Meruelo, L. Liebes, Y. Mazur, E. Dubovi, M. Mandel, G. Lavie, Photochem. Photobiol. 2000, 71, 188.
- (2000) Photochem. Photobiol. , vol.71 , pp. 188
- Prince, A.M.¹ Pascual, D.² Meruelo, D.³ Liebes, L.⁴ Mazur, Y.⁵ Dubovi, E.⁶ Mandel, M.⁷ Lavie, G.⁸

5
- 0003543593
- VCH, New York, p.
- R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 685
- (1989) Comprehensive Organic Transformations , pp. 685
- Larock, R.C.¹

6
- 0003467672
- 3rd ed. Wiley, New York, and 824-827.
- J. March, Advanced Organic Chemistry, 3rd ed., Wiley, New York, 1985, pp. 433-435 and 824-827.
- (1985) Advanced Organic Chemistry , pp. 433-435
- March, J.¹

7
- 33947346424
- H. Gilman, P. R. vanEss, J. Am. Chem. Soc. 1933, 55, 1258
- (1933) J. Am. Chem. Soc. , vol.55 , pp. 1258
- Gilman, H.¹ Vaness, P.R.²

8
- 0001356064
- K. Mislow, J. Brenner, J. Am. Chem. Soc. 1953, 75, 2318
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 2318
- Mislow, K.¹ Brenner, J.²

9
- 0001303127
- R. Levine, M. J. Karten, W. M. Kadunce, J. Org. Chem. 1975, 40, 1770
- (1975) J. Org. Chem. , vol.40 , pp. 1770
- Levine, R.¹ Karten, M.J.² Kadunce, W.M.³

10
- 0001447154
- W. D. Lubell, H. Rapoport, J. Am. Chem. Soc. 1988, 110, 7447
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 7447
- Lubell, W.D.¹ Rapoport, H.²

11
- 84869820151
- S. Daum, F. Erdmann, G. Fischer, B. F. Lacroix, A. Hessamian-Alinejad, S. Houben, W. Frank, M. Braun, Angew. Chem. 2006, 118, 7615
- (2006) Angew. Chem. , vol.118 , pp. 7615
- Daum, S.¹ Erdmann, F.² Fischer, G.³ Lacroix, B.F.⁴ Hessamian-Alinejad, A.⁵ Houben, S.⁶ Frank, W.⁷ Braun, M.⁸

12
- 33751234234
- Angew. Chem. Int. Ed. 2006, 45, 7454
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7454

13
- 80054754263
- D. R. Genna, G. H. Posner, Org. Lett. 2011, 13, 5358.
- (2011) Org. Lett. , vol.13 , pp. 5358
- Genna, D.R.¹ Posner, G.H.²

14
- 0004918028
- G. Zadel, E. Breitmaier, Angew. Chem. 1992, 104, 1070
- (1992) Angew. Chem. , vol.104 , pp. 1070
- Zadel, G.¹ Breitmaier, E.²

15
- 33748239740
- Angew. Chem. Int. Ed. Engl. 1992, 31, 1035.
- (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1035

16
- 34447102805
- T. Sakakura, J. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365
- (2007) Chem. Rev. , vol.107 , pp. 2365
- Sakakura, T.¹ Choi, J.² Yasuda, H.³

17
- 84856524789
- M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Kühn, Angew. Chem. 2011, 123, 8662
- (2011) Angew. Chem. , vol.123 , pp. 8662
- Cokoja, M.¹ Bruckmeier, C.² Rieger, B.³ Herrmann, W.A.⁴ Kühn, F.E.⁵

18
- 80052445289
- Angew. Chem. Int. Ed. 2011, 50, 8510
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 8510

19
- 84860881935
- I. Omae, Coord. Chem. Rev. 2012, 256, 1384.
- (2012) Coord. Chem. Rev. , vol.256 , pp. 1384
- Omae, I.¹

20
- 0006674249
- E. J. Soloski, C. Tamborski, J. Organomet. Chem. 1978, 157, 373
- (1978) J. Organomet. Chem. , vol.157 , pp. 373
- Soloski, E.J.¹ Tamborski, C.²

21
- 0000665936
- M. A. Peterson, J. R. Mitchell, J. Org. Chem. 1997, 62, 8237
- (1997) J. Org. Chem. , vol.62 , pp. 8237
- Peterson, M.A.¹ Mitchell, J.R.²

22
- 0035213223
- J. C. Anderson, S. Broughton, Synthesis 2001, 2379.
- (2001) Synthesis , pp. 2379
- Anderson, J.C.¹ Broughton, S.²

23
- 84887166938
- J. C. Pastre, D. L. Browne, S. V. Ley, Chem. Soc. Rev. 2013, 42, 8849
- (2013) Chem. Soc. Rev. , vol.42 , pp. 8849
- Pastre, J.C.¹ Browne, D.L.² Ley, S.V.³

24
- 84885086350
- J. Yoshida, Y. Takahashi, A. Nagaki, Chem. Commun. 2013, 49, 9896
- (2013) Chem. Commun. , vol.49 , pp. 9896
- Yoshida, J.¹ Takahashi, Y.² Nagaki, A.³

25
- 84880034053
- D. T. McQuade, P. H. Seeberger, J. Org. Chem. 2013, 78, 6384
- (2013) J. Org. Chem. , vol.78 , pp. 6384
- McQuade, D.T.¹ Seeberger, P.H.²

26
- 84862084481
- N. G. Anderson, Org. Process Res. Dev. 2012, 16, 852
- (2012) Org. Process Res. Dev. , vol.16 , pp. 852
- Anderson, N.G.¹

27
- 80054031755
- R. L. Hartman, J. P. McMullen, K. F. Jensen, Angew. Chem. 2011, 123, 7642
- (2011) Angew. Chem. , vol.123 , pp. 7642
- Hartman, R.L.¹ McMullen, J.P.² Jensen, K.F.³

28
- 79961218749
- Angew. Chem. Int. Ed. 2011, 50, 7502
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7502

29
- 79551614063
- D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675
- (2010) Chem. Sci. , vol.1 , pp. 675
- Webb, D.¹ Jamison, T.F.²

30
- 77952935876
- T. Razzaq, C. O. Kappe, Chem. Asian J. 2010, 5, 1274.
- (2010) Chem. Asian J. , vol.5 , pp. 1274
- Razzaq, T.¹ Kappe, C.O.²

31
- 84904557759
- Z. He, T. F. Jamison, Angew. Chem. 2014, 126, 3421
- (2014) Angew. Chem. , vol.126 , pp. 3421
- He, Z.¹ Jamison, T.F.²

32
- 84896445415
- Angew. Chem. Int. Ed. 2014, 53, 3353
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 3353

33
- 84893492955
- J. Wu, J. A. Kozak, F. Simeon, T. A. Hatton, T. F. Jamison, Chem. Sci. 2014, 5, 1227
- (2014) Chem. Sci. , vol.5 , pp. 1227
- Wu, J.¹ Kozak, J.A.² Simeon, F.³ Hatton, T.A.⁴ Jamison, T.F.⁵

34
- 84890451910
- J. A. Kozak, J. Wu, X. Su, F. Simeon, T. A. Hatton, T. F. Jamison, J. Am. Chem. Soc. 2013, 135, 18497
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 18497
- Kozak, J.A.¹ Wu, J.² Su, X.³ Simeon, F.⁴ Hatton, T.A.⁵ Jamison, T.F.⁶

35
- 84878809904
- D. R. Snead, T. F. Jamison, Chem. Sci. 2013, 4, 2822
- (2013) Chem. Sci. , vol.4 , pp. 2822
- Snead, D.R.¹ Jamison, T.F.²

36
- 84887882861
- Y. Zhang, M. L. Blackman, A. B. Leduc, T. F. Jamison, Angew. Chem. 2013, 125, 4345
- (2013) Angew. Chem. , vol.125 , pp. 4345
- Zhang, Y.¹ Blackman, M.L.² Leduc, A.B.³ Jamison, T.F.⁴

37
- 84875837033
- Angew. Chem. Int. Ed. 2013, 52, 4251.
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4251

38
- 2542543730
- J. Kobayashi, Y. Mori, K. Okamoto, R. Akiama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305
- (2004) Science , vol.304 , pp. 1305
- Kobayashi, J.¹ Mori, Y.² Okamoto, K.³ Akiama, R.⁴ Ueno, M.⁵ Kitamori, T.⁶ Kobayashi, S.⁷

39
- 33744494551
- M. T. Rahman, T. Fukuyama, N. Kamata, M. Sato, I. Ryu, Chem. Commun. 2006, 2236
- (2006) Chem. Commun. , pp. 2236
- Rahman, M.T.¹ Fukuyama, T.² Kamata, N.³ Sato, M.⁴ Ryu, I.⁵

40
- 79959270622
- A. Polyzos, M. O'Brien, T. P. Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. 2011, 123, 1222
- (2011) Angew. Chem. , vol.123 , pp. 1222
- Polyzos, A.¹ O'Brien, M.² Petersen, T.P.³ Baxendale, I.R.⁴ Ley, S.V.⁵

41
- 79251535032
- Angew. Chem. Int. Ed. 2011, 50, 1190
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 1190

42
- 80054728059
- F. Lévesque, P. H. Seeberger, Org. Lett. 2011, 13, 5008
- (2011) Org. Lett. , vol.13 , pp. 5008
- Lévesque, F.¹ Seeberger, P.H.²

43
- 84896460302
- B. Pieber, S. T. Martinez, D. Cantillo, C. O. Kappe, Angew. Chem. 2013, 125, 10431
- (2013) Angew. Chem. , vol.125 , pp. 10431
- Pieber, B.¹ Martinez, S.T.² Cantillo, D.³ Kappe, C.O.⁴

44
- 84884825779
- Angew. Chem. Int. Ed. 2013, 52, 10241
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 10241

45
- 84922803955
- D. B. Ushakov, K. Gilmore, D. Kopetzki, D. T. McQuade, P. H. Seeberger, Angew. Chem. 2014, 126, 568
- (2014) Angew. Chem. , vol.126 , pp. 568
- Ushakov, D.B.¹ Gilmore, K.² Kopetzki, D.³ McQuade, D.T.⁴ Seeberger, P.H.⁵

46
- 84891809503
- Angew. Chem. Int. Ed. 2014, 53, 557.
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 557

47
- 33947317243
- House and Bare have shown that quenching the batch reaction by removing aliquots from reaction mixtures and adding them dropwise to ice and dilute hydrochloric acid with vigorous stirring can effectively avoid alcohol byproduct formation, see.
- House and Bare have shown that quenching the batch reaction by removing aliquots from reaction mixtures and adding them dropwise to ice and dilute hydrochloric acid with vigorous stirring can effectively avoid alcohol byproduct formation, see:, H. O. House, T. M. Bare, J. Org. Chem. 1968, 33, 943.
- (1968) J. Org. Chem. , vol.33 , pp. 943
- House, H.O.¹ Bare, T.M.²

48
- 84896368207
- B. Pieber, T. Glasnov, C. O. Kappe, RSC Adv. 2014, 4, 13430
- (2014) RSC Adv. , vol.4 , pp. 13430
- Pieber, B.¹ Glasnov, T.² Kappe, C.O.³

49
- 84905390377
- DOI.
- A. Nagaki, Y. Takahashi, J.-i. Yoshida, Chem. Eur. J. 2014, DOI:.
- (2014) Chem. Eur. J.
- Nagaki, A.¹ Takahashi, Y.² Yoshida, J.-I.³

50
- 0000594678
- R. Waack, M. A. Doran, J. Organomet. Chem. 1971, 29, 329.
- (1971) J. Organomet. Chem. , vol.29 , pp. 329
- Waack, R.¹ Doran, M.A.²

51
- 32344433949
- Elsevier, Amsterdam, p..
- L. Kürti, B. Czakõ, Strategic Applications of Named Reactions in Organic Synthesis, Elsevier, Amsterdam, 2005, p. 176.
- (2005) Strategic Applications of Named Reactions in Organic Synthesis , pp. 176
- Kürti, L.¹ Czakõ, B.²

52
- 0037036757
- M. A. Evans, J. P. Morken, J. Am. Chem. Soc. 2002, 124, 9020
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 9020
- Evans, M.A.¹ Morken, J.P.²

53
- 6444238093
- Y. Tsuji, M. M. Oteva, T. L. Amyes, J. P. Richard, Org. Lett. 2004, 6, 3633
- (2004) Org. Lett. , vol.6 , pp. 3633
- Tsuji, Y.¹ Oteva, M.M.² Amyes, T.L.³ Richard, J.P.⁴

54
- 67249094058
- O. Khdour, E. Skibo, Org. Biomol. Chem. 2009, 7, 2140
- (2009) Org. Biomol. Chem. , vol.7 , pp. 2140
- Khdour, O.¹ Skibo, E.²

55
- 77955800923
- P. Lehwald, M. Richter, C. Röhr, H. Liu, M. Müller, Angew. Chem. 2010, 122, 2439
- (2010) Angew. Chem. , vol.122 , pp. 2439
- Lehwald, P.¹ Richter, M.² Röhr, C.³ Liu, H.⁴ Müller, M.⁵

56
- 77952956848
- Angew. Chem. Int. Ed. 2010, 49, 2389.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2389

57
- 0001630249
- For half-lives of organolithium reagents in common ethereal solvents, see:, P. Stanetty, M. D. Mihovilovic, J. Org. Chem. 1997, 62, 1514; For more details of observed results, see the Supporting Information.
- (1997) J. Org. Chem. , vol.62 , pp. 1514
- Stanetty, P.¹ Mihovilovic, M.D.²

58
- 0001126819
- V. Grignard, Hebd. Seances Acad. Sci. 1900, 130, 1322.
- (1900) Hebd. Seances Acad. Sci. , vol.130 , pp. 1322
- Grignard, V.¹

59
- 0001141847
- V. Fiandanese, G. Marchese, L. Ronzini, Tetrahedron Lett. 1983, 24, 3677
- (1983) Tetrahedron Lett. , vol.24 , pp. 3677
- Fiandanese, V.¹ Marchese, G.² Ronzini, L.³

60
- 0001522954
- T. Fujisawa, T. Mori, T. Sato, Tetrahedron Lett. 1982, 23, 5059.
- (1982) Tetrahedron Lett. , vol.23 , pp. 5059
- Fujisawa, T.¹ Mori, T.² Sato, T.³

61
- 0001519904
- For a report on the generation of ketones from α-amino carboxylithium and Grignard reagents, see:, C. G. Knudsen, H. Rapoport, J. Org. Chem. 1983, 48, 2260
- (1983) J. Org. Chem. , vol.48 , pp. 2260
- Knudsen, C.G.¹ Rapoport, H.²

62
- 0035843432
- For a report on the generation of ketones from carboxylic acids using Grignard reagents with the aid of N-protecting groups, see:, P. Zhang, E. A. Terefenko, J. Slavin, Tetrahedron Lett. 2001, 42, 2097.
- (2001) Tetrahedron Lett. , vol.42 , pp. 2097
- Zhang, P.¹ Terefenko, E.A.² Slavin, J.³

63
- 65249184090
- A. Nagaki, H. Kim, J. Yoshida, Angew. Chem. 2008, 120, 7951
- (2008) Angew. Chem. , vol.120 , pp. 7951
- Nagaki, A.¹ Kim, H.² Yoshida, J.³

64
- 54749106512
- Angew. Chem. Int. Ed. 2008, 47, 7833
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7833

65
- 79953769993
- H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2, 264
- (2011) Nat. Commun. , vol.2 , pp. 264
- Kim, H.¹ Nagaki, A.² Yoshida, J.³

66
- 84875332548
- A. Nagaki, Y. Uesugi, H. Kim, J. Yoshida, Chem. Asian J. 2013, 8, 705
- (2013) Chem. Asian J. , vol.8 , pp. 705
- Nagaki, A.¹ Uesugi, Y.² Kim, H.³ Yoshida, J.⁴

67
- 84884599019
- P. R. D. Murray, D. L. Browne, J. C. Pastre, C. Butters, D. Guthrie, S. V. Ley, Org. Process Res. Dev. 2013, 15, 1192.
- (2013) Org. Process Res. Dev. , vol.15 , pp. 1192
- Murray, P.R.D.¹ Browne, D.L.² Pastre, J.C.³ Butters, C.⁴ Guthrie, D.⁵ Ley, S.V.⁶

68
- 84862064868
- T. Brodmann, P. Koos, A. Metzger, P. Knochel, S. V. Ley, Org. Process Res. Dev. 2012, 16, 1102
- (2012) Org. Process Res. Dev. , vol.16 , pp. 1102
- Brodmann, T.¹ Koos, P.² Metzger, A.³ Knochel, P.⁴ Ley, S.V.⁵

69
- 77953141036
- T. Tricotet, D. F. O'Shea, Chem. Eur. J. 2010, 16, 6678
- (2010) Chem. Eur. J. , vol.16 , pp. 6678
- Tricotet, T.¹ O'Shea, D.F.²

70
- 28944448747
- H. Wakami, J. Yoshida, Org. Process Res. Dev. 2005, 9, 787.
- (2005) Org. Process Res. Dev. , vol.9 , pp. 787
- Wakami, H.¹ Yoshida, J.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.