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Organic Letters

Volumn 6, Issue 9, 2004, Pages 1473-1476

A highly efficient microwave-assisted Suzuki coupling reaction of aryl perfluorooctylsulfonates with boronic acids

(4) Zhang, Wei a Chen, Christine Hiu Tung a Lu, Yimin a Nagashima, Tadamichi a

a UNIVERSITY OF PITTSBURGH (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; HYDANTOIN DERIVATIVE; PHENOL DERIVATIVE; SILICA GEL; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; SOLID PHASE EXTRACTION; SUZUKI REACTION; SYNTHESIS;

ALKANESULFONIC ACIDS; BORONIC ACIDS; FLUOROCARBONS; HYDROCARBONS, FLUORINATED; MICROWAVES; MOLECULAR STRUCTURE; SULFATES;

EID: 2442445175 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0496428 Document Type: Article

Times cited : (102)

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17
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- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1071
- Brase, S.¹ Schroen, M.²

18
- 0034595263
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- Vanier, Y.¹ Lorge, F.² Wagner, A.³ Mioskowski, C.⁴

19
- 0000403742
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- Pourbaix, C.¹ Carreaux, F.² Carboni, B.³

20
- 0000892037
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21
- 0344666674
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- Lan, P.¹ Berta, D.² Porco, J.A.³ South, M.S.⁴ Parlow, J.J.⁵

22
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- (2003) J. Comb. Chem. , vol.5 , pp. 118
- Organ, M.G.¹ Mayer, S.²

23
- 0038520755
- Selected papers: (a) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527 (b) Brase, S.; Schroen, M. Angew. Chem., Int. Ed. 1999, 38, 1071. (c) Vanier, Y.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679. (d) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803. (e) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami Org. Lett. 2002, 4, 3371. (f) Lan, P.; Berta, D.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678. (g) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118. (h) Wade, J. V.; Krueger, C. A. J. Comb. Chem. 2003, 5, 267. (i) Zhu, S.; Shi, S.; Gerritz, S. W.; Sofia, M. J. J. Comb. Chem. 2003, 5, 205. (j) Byun, J.-W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837. See also general reviews: (k) Negishi, E., Ed. Hankbook of Palladium Chemistry; Wiley: New York, 2002. (l) Lorsbury, B. A.; Kurt, M. J. Chem. Rev. 1999, 99, 1549. (m) Brase, S.; Kirchhoff, J. H.; Kobberling, J. Tetrahedron 2003, 59, 885.
- (2003) J. Comb. Chem. , vol.5 , pp. 267
- Wade, J.V.¹ Krueger, C.A.²

24
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- (2003) J. Comb. Chem. , vol.5 , pp. 205
- Zhu, S.¹ Shi, S.² Gerritz, S.W.³ Sofia, M.J.⁴

25
- 1242271378
- Selected papers: (a) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527 (b) Brase, S.; Schroen, M. Angew. Chem., Int. Ed. 1999, 38, 1071. (c) Vanier, Y.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679. (d) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803. (e) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami Org. Lett. 2002, 4, 3371. (f) Lan, P.; Berta, D.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678. (g) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118. (h) Wade, J. V.; Krueger, C. A. J. Comb. Chem. 2003, 5, 267. (i) Zhu, S.; Shi, S.; Gerritz, S. W.; Sofia, M. J. J. Comb. Chem. 2003, 5, 205. (j) Byun, J.-W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837. See also general reviews: (k) Negishi, E., Ed. Hankbook of Palladium Chemistry; Wiley: New York, 2002. (l) Lorsbury, B. A.; Kurt, M. J. Chem. Rev. 1999, 99, 1549. (m) Brase, S.; Kirchhoff, J. H.; Kobberling, J. Tetrahedron 2003, 59, 885.
- (2004) Tetrahedron Lett. , vol.45 , pp. 1837
- Byun, J.-W.¹ Lee, Y.S.²

26
- 0347725853
- Wiley: New York
- Selected papers: (a) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527 (b) Brase, S.; Schroen, M. Angew. Chem., Int. Ed. 1999, 38, 1071. (c) Vanier, Y.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679. (d) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803. (e) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami Org. Lett. 2002, 4, 3371. (f) Lan, P.; Berta, D.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678. (g) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118. (h) Wade, J. V.; Krueger, C. A. J. Comb. Chem. 2003, 5, 267. (i) Zhu, S.; Shi, S.; Gerritz, S. W.; Sofia, M. J. J. Comb. Chem. 2003, 5, 205. (j) Byun, J.-W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837. See also general reviews: (k) Negishi, E., Ed. Hankbook of Palladium Chemistry; Wiley: New York, 2002. (l) Lorsbury, B. A.; Kurt, M. J. Chem. Rev. 1999, 99, 1549. (m) Brase, S.; Kirchhoff, J. H.; Kobberling, J. Tetrahedron 2003, 59, 885.
- (2002) Hankbook of Palladium Chemistry
- Negishi, E.¹

27
- 0001246358
- Selected papers: (a) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527 (b) Brase, S.; Schroen, M. Angew. Chem., Int. Ed. 1999, 38, 1071. (c) Vanier, Y.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2000, 39, 1679. (d) Pourbaix, C.; Carreaux, F.; Carboni, B. Org. Lett. 2001, 3, 803. (e) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami Org. Lett. 2002, 4, 3371. (f) Lan, P.; Berta, D.; Porco, J. A.; South, M. S.; Parlow, J. J. J. Org. Chem. 2003, 68, 9678. (g) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118. (h) Wade, J. V.; Krueger, C. A. J. Comb. Chem. 2003, 5, 267. (i) Zhu, S.; Shi, S.; Gerritz, S. W.; Sofia, M. J. J. Comb. Chem. 2003, 5, 205. (j) Byun, J.-W.; Lee, Y. S. Tetrahedron Lett. 2004, 45, 1837. See also general reviews: (k) Negishi, E., Ed. Hankbook of Palladium Chemistry; Wiley: New York, 2002. (l) Lorsbury, B. A.; Kurt, M. J. Chem. Rev. 1999, 99, 1549. (m) Brase, S.; Kirchhoff, J. H.; Kobberling, J. Tetrahedron 2003, 59, 885.
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28
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44
- 2442529996
- note
- 4, and the solvent was evaporated under vacuum to give perfluorooctylsulfonate 1a (9.79 g, 91% yield). The crude product was used for the next step. It can be further purified by recrystallization with MeOH or by F-SPE.

45
- 2442452823
- 17 stationary phase. For more information about F-SPE, please log on to http://www.fluorous.com/download/fspe. pdf.

46
- 2442483963
- note
- 1 H NMR.

47
- 0032512011
- Pridgen, L. N.; Huang, G. K. Tetrahedron Lett. 1998, 39, 8421.
- (1998) Tetrahedron Lett. , vol.39 , pp. 8421
- Pridgen, L.N.¹ Huang, G.K.²

48
- 2442496515
- note
- 2O. The fraction was concentrated to give biaryl 2a (27.6 mg, 91% yield). The fluorous species were washed from the cartridge with 20 mL of MeOH.

49
- 2442584779
- note
- Pd-catalyzed microwave reactions were conducted under a license from Personal Chemistry.

50
- 2442631701
- note
- No further quantitative analysis has been attempted to detect the residue of catalyst and ligand in final products.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.