SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn , Issue 37, 2006, Pages 3883-3885

Copper catalyzed oxidation of organozinc halides

(5) Su, Xianbin a Fox, David J a Blackwell, David T a Tanaka, Kiyotaka a Spring, David R a

a UNIVERSITY OF CAMBRIDGE (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COPPER; HALIDE; ORGANIC COMPOUND; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; OXIDATION;

EID: 33748879772 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b610218b Document Type: Article

Times cited : (29)

References (45)

1
- 0036589259
- J. Hassan M. Sévignon C. Gozzi E. Sculz M. Lemaire Chem. Rev. 2002 102 1359
- (2002) Chem. Rev. , vol.102 , pp. 1359
- Hassan, J.¹ Sévignon, M.² Gozzi, C.³ Sculz, E.⁴ Lemaire, M.⁵

2
- 11444254369
- W. Su S. Urgaonkar P. M. McLaughlin J. G. Verkade J. Am. Chem. Soc. 2004 126 16433
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 16433
- Su, W.¹ Urgaonkar, S.² McLaughlin, P.M.³ Verkade, J.G.⁴

3
- 9344240844
- G. Altenhoff R. Goddard C. W. Lehmann F. Glorius J. Am. Chem. Soc. 2004 126 15195
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 15195
- Altenhoff, G.¹ Goddard, R.² Lehmann, C.W.³ Glorius, F.⁴

4
- 5644254180
- J. E. Milne S. L. Buchwald J. Am. Chem. Soc. 2004 126 13028
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 13028
- Milne, J.E.¹ Buchwald, S.L.²

5
- 1942501106
- A. N. Cammidge K. V. L. Crépy Tetrahedron 2004 60 4377
- (2004) Tetrahedron , vol.60 , pp. 4377
- Cammidge, A.N.¹ Crépy, K.V.L.²

6
- 0034812321
- C. Dai G. C. Fu J. Am. Chem. Soc. 2001 123 2719
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 2719
- Dai, C.¹ Fu, G.C.²

7
- 85065137145
- For a recent application see
- P. E. Fanta Synthesis 1974 9
- (1974) Synthesis , pp. 9
- Fanta, P.E.¹

8
- 1942436903
- A. I. Meyers T. D. Nelson H. Moorlag D. J. Rawson A. Meier Tetrahedron 2004 60 4459
- (2004) Tetrahedron , vol.60 , pp. 4459
- Meyers, A.I.¹ Nelson, T.D.² Moorlag, H.³ Rawson, D.J.⁴ Meier, A.⁵

9
- 0034817381
- R. Hong R. Hoen J. Zhang G. Lin Synlett 2001 1527
- (2001) Synlett , pp. 1527
- Hong, R.¹ Hoen, R.² Zhang, J.³ Lin, G.⁴

10
- 33845557330
- M. F. Semmelhack P. Helquist L. D. Jones L. Keller L. Mendelson L. S. Ryono J. G. Smith R. D. Stauffer J. Am. Chem. Soc. 1981 103 6461
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 6461
- Semmelhack, M.F.¹ Helquist, P.² Jones, L.D.³ Keller, L.⁴ Mendelson, L.⁵ Ryono, L.S.⁶ Smith, J.G.⁷ Stauffer, R.D.⁸

11
- 0034851484
- K. Khanbabaee T. van Ree Synthesis 2001 1585
- (2001) Synthesis , pp. 1585
- Khanbabaee, K.¹ Van Ree, T.²

12
- 0001308223
- S. Quideau K. S. Feldman Chem. Rev. 1996 96 475
- (1996) Chem. Rev. , vol.96 , pp. 475
- Quideau, S.¹ Feldman, K.S.²

13
- 0028272405
- T. D. Nelson A. I. Meyers J. Org. Chem. 1994 59 2577
- (1994) J. Org. Chem. , vol.59 , pp. 2577
- Nelson, T.D.¹ Meyers, A.I.²

14
- 33748851818
- I. A. O'Neil, Thieme, Stuttgart, 305
- H. Heany and S. Christie, in Science of Synthesis, ed., I. A. O'Neil,, Thieme, Stuttgart, 2004, vol. 3, p. 305
- (2004) Science of Synthesis, Ed. , vol.3
- Heany, H.¹ Christie In, S.²

15
- 0004246896
- N. Krause, Wiley-VCH, Weinheim
- Modern Organocopper Chemistry, ed., N. Krause,, Wiley-VCH, Weinheim, 2002
- (2002) Modern Organocopper Chemistry, Ed.

16
- 33748862549
- R. J. K. Taylor, Series ed. L. M. Harwood and C. J. Moody, Oxford University Press, Oxford
- Organocopper Reagents - A Practical Approach, ed., R. J. K. Taylor,, Series ed., L. M. Harwood and C. J. Moody,, Oxford University Press, Oxford, 1994
- (1994) Organocopper Reagents - A Practical Approach, Ed.

17
- 33947337524
- For low temperature cross-coupling, see
- G. M. Whitesides J. SanFilippo, Jr. C. P. Casey E. P. Panek J. Am. Chem. Soc. 1967 89 5302
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 5302
- Whitesides, G.M.¹ SanFilippo Jr., J.² Casey, C.P.³ Panek, E.P.⁴

18
- 0346471289
- For intramolecular coupling, see:
- B. H. Lipshutz K. Siegmann E. Garcia F. Kayser J. Am. Chem. Soc. 1993 115 9276
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 9276
- Lipshutz, B.H.¹ Siegmann, K.² Garcia, E.³ Kayser, F.⁴

19
- 33748222146
- For cross-coupling of lithium dialkylcuprates, see:
- B. H. Lipshutz F. Kayser Z.-P. Liu Angew. Chem., Int. Ed. Engl. 1994 33 1842
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1842
- Lipshutz, B.H.¹ Kayser, F.² Liu, Z.-P.³

20
- 1842789668
- For selected applications see:
- R. K. Dieter S. Li H. Chen J. Org. Chem. 2004 69 2867
- (2004) J. Org. Chem. , vol.69 , pp. 2867
- Dieter, R.K.¹ Li, S.² Chen, H.³

21
- 18844438606
- R. S. Coleman S. R. Gurrala Org. Lett. 2005 7 1849
- (2005) Org. Lett. , vol.7 , pp. 1849
- Coleman, R.S.¹ Gurrala, S.R.²

22
- 0037138650
- D. R. Spring S. Krishnan H. E. Blackwell S. L. Schreiber J. Am. Chem. Soc. 2002 124 1354
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1354
- Spring, D.R.¹ Krishnan, S.² Blackwell, H.E.³ Schreiber, S.L.⁴

23
- 0001431117
- R. W. Baker R. V. Kyasnoor M. V. Sargent B. W. Skelton A. H. White Aust. J. Chem. 2000 53 487
- (2000) Aust. J. Chem. , vol.53 , pp. 487
- Baker, R.W.¹ Kyasnoor, R.V.² Sargent, M.V.³ Skelton, B.W.⁴ White, A.H.⁵

24
- 0000089379
- For a recent review see:
- M. B. Andrus D. Asgari J. A. Sclafani J. Org. Chem. 1997 62 9365
- (1997) J. Org. Chem. , vol.62 , pp. 9365
- Andrus, M.B.¹ Asgari, D.² Sclafani, J.A.³

25
- 33644642918
- D. S. Surry D. R. Spring Chem. Soc. Rev. 2006 35 218
- (2006) Chem. Soc. Rev. , vol.35 , pp. 218
- Surry, D.S.¹ Spring, D.R.²

26
- 17044379486
- D. S. Surry X. Su D. J. Fox V. Franckevicius S. J. F. Macdonald D. R. Spring Angew. Chem., Int. Ed. 2005 44 1870
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1870
- Surry, D.S.¹ Su, X.² Fox, D.J.³ Franckevicius, V.⁴ MacDonald, S.J.F.⁵ Spring, D.R.⁶

27
- 33748876548
- and references therein For the oxidation of zinc amidocuprates in the formation of carbon-nitrogen bonds, see:
- I. Hiriyakkanavar O. Baron A. J. Wagner P. Knochel Chem. Commun. 2006 583
- (2006) Chem. Commun. , pp. 583
- Hiriyakkanavar, I.¹ Baron, O.² Wagner, A.J.³ Knochel, P.⁴

28
- 0030917964
- F. Canè D. Brancaleoni P. Dembech A. Ricci G. Seconi Synthesis 1997 545
- (1997) Synthesis , pp. 545
- Canè, F.¹ Brancaleoni, D.² Dembech, P.³ Ricci, A.⁴ Seconi, G.⁵

29
- 4243489506
- P. Knochel R. D. Singer Chem. Rev. 1993 93 2117
- (1993) Chem. Rev. , vol.93 , pp. 2117
- Knochel, P.¹ Singer, R.D.²

30
- 0027271839
- P. Wipf Synthesis 1993 537
- (1993) Synthesis , pp. 537
- Wipf, P.¹

31
- 0000358709
- L. Zhu R. M. Wehmeyer R. D. Rieke J. Org. Chem. 1991 56 1445
- (1991) J. Org. Chem. , vol.56 , pp. 1445
- Zhu, L.¹ Wehmeyer, R.M.² Rieke, R.D.³

32
- 0037414264
- H. Fillon C. Gosmini J. Périchon J. Am. Chem. Soc. 2003 125 3867
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 3867
- Fillon, H.¹ Gosmini, C.² Périchon, J.³

33
- 0025369168
- T. N. Majid P. Knochel Tetrahedron Lett. 1990 31 4413
- (1990) Tetrahedron Lett. , vol.31 , pp. 4413
- Majid, T.N.¹ Knochel, P.²

34
- 0037459750
- R. Ikegami A. Koresawa T. Shibata K. Takagi J. Org. Chem. 2003 68 2195
- (2003) J. Org. Chem. , vol.68 , pp. 2195
- Ikegami, R.¹ Koresawa, A.² Shibata, T.³ Takagi, K.⁴

35
- 33748851460
- Other solvents can be used, such as THF, MeCN; however, yields were highest using DMA
- Other solvents can be used, such as THF, MeCN; however, yields were highest using DMA

36
- 33748878357
- Further decreases in the amount of copper reduced the yield marginally
- Further decreases in the amount of copper reduced the yield marginally

37
- 33748851299
- Electron-rich systems, for example 4-bromoanisole, required 0.25 equivalents of oxidant per aryl zinc; whereas electron-poor systems, for example ethyl 4-bromobenzoate, required 0.5 equivalents of oxidant per aryl zinc. This disparity may reflect the differences in the energy of the HOMO of the respective zinc organocuprates
- Electron-rich systems, for example 4-bromoanisole, required 0.25 equivalents of oxidant per aryl zinc; whereas electron-poor systems, for example ethyl 4-bromobenzoate, required 0.5 equivalents of oxidant per aryl zinc. This disparity may reflect the differences in the energy of the HOMO of the respective zinc organocuprates

38
- 37049068125
- M. Takahashi T. Ogiku T. Okamura T. Da-te H. Ohmizu K. Kondo T. Iwasaki J. Chem. Soc., Perkin Trans. 1 1993 1473
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 1473
- Takahashi, M.¹ Ogiku, T.² Okamura, T.³ Da-Te, T.⁴ Ohmizu, H.⁵ Kondo, K.⁶ Iwasaki, T.⁷

39
- 0028794812
- For syntheses of buflavine, see:
- F. Viladomat J. Bastida C. Codina W. E. Campbell S. Mathee Phytochemistry 1995 40 307
- (1995) Phytochemistry , vol.40 , pp. 307
- Viladomat, F.¹ Bastida, J.² Codina, C.³ Campbell, W.E.⁴ Mathee, S.⁵

40
- 2342485821
- S. Kodama H. Takita T. Kajimoto K. Nishide M. Node Tetrahedron 2004 60 4901
- (2004) Tetrahedron , vol.60 , pp. 4901
- Kodama, S.¹ Takita, H.² Kajimoto, T.³ Nishide, K.⁴ Node, M.⁵

41
- 0037670114
- P. Sahakitpichan S. Ruchirawat Tetrahedron Lett. 2003 44 5239
- (2003) Tetrahedron Lett. , vol.44 , pp. 5239
- Sahakitpichan, P.¹ Ruchirawat, S.²

42
- 0037047545
- C. Hoarau A. Couture E. Deniau P. Grandclaudon J. Org. Chem. 2002 67 5846
- (2002) J. Org. Chem. , vol.67 , pp. 5846
- Hoarau, C.¹ Couture, A.² Deniau, E.³ Grandclaudon, P.⁴

43
- 0032510436
- P. A. Patil V. Snieckus Tetrahedron Lett. 1998 39 1325
- (1998) Tetrahedron Lett. , vol.39 , pp. 1325
- Patil, P.A.¹ Snieckus, V.²

44
- 0017587697
- (synthesis coincidentally predates the isolation and structural elucidation of buflavine) For the synthesis of buflavine analogues, see:
- S. Kobayashi S. Kihara S. Shizu S. Katayama H. Ikeda K. Kitahiro H. Matsumoto Chem. Pharm. Bull. 1977 25 3312
- (1977) Chem. Pharm. Bull. , vol.25 , pp. 3312
- Kobayashi, S.¹ Kihara, S.² Shizu, S.³ Katayama, S.⁴ Ikeda, H.⁵ Kitahiro, K.⁶ Matsumoto, H.⁷

45
- 27744447605
- P. Appukkuttan W. Dehaen E. V. Eycken Org. Lett. 2005 7 2723
- (2005) Org. Lett. , vol.7 , pp. 2723
- Appukkuttan, P.¹ Dehaen, W.² Eycken, E.V.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.