SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 11, Issue 13, 2009, Pages 2860-2863

Fluorination of boronic acids mediated by silver(I) Triflate

(2) Furuya, Takeru a Ritter, Toblas a

a HARVARD UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; ESTER; MESYLIC ACID DERIVATIVE; SILVER; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; STEREOISOMERISM;

BORONIC ACIDS; CATALYSIS; ESTERS; HALOGENATION; MESYLATES; MOLECULAR STRUCTURE; SILVER; STEREOISOMERISM;

EID: 67649467487 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol901113t Document Type: Article

Times cited : (245)

References (36)

1
- 67649552512
- (a) Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214231.
- (2005) Angew. Chem., Int. Ed , vol.44 , pp. 214231
- Shimizu, M.¹ Hiyama, T.²

2
- 67649571997
- Lasne, M. C.; Perrio, C.; Rouden, J.; Barre, L.; Roeda, D.; Dolle, F.; Crouzel, C. Chemistry of beta(+)-emitting compounds based on fluorine18. In. Contrast Agents II 2002, 222, 201-258.
- (b) Lasne, M. C.; Perrio, C.; Rouden, J.; Barre, L.; Roeda, D.; Dolle, F.; Crouzel, C. Chemistry of beta(+)-emitting compounds based on fluorine18. In. Contrast Agents II 2002, 222, 201-258.

3
- 4544369746
- (c) Jeschke, P. ChemBioChem 2004, 5, 570-589.
- (2004) ChemBioChem , vol.5 , pp. 570-589
- Jeschke, P.¹

4
- 84869305504
- Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 18811886.
- (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 18811886.

5
- 0004098366
- Oxford: New York
- (a) Chambers, R. D. Fluorine in organic chemistry; Oxford: New York, 2004.
- (2004) Fluorine in organic chemistry
- Chambers, R.D.¹

6
- 54549103372
- (b) Furuya, T.; Kuttruff, C. A.; Ritter, T Curr. Opin. Drug. Discovery Dev. 2008, 11, 803-819.
- (2008) Curr. Opin. Drug. Discovery Dev , vol.11 , pp. 803-819
- Furuya, T.¹ Kuttruff, C.A.² Ritter, T.³

7
- 64349105617
- Baudoux, J; Cahard, D. Org. React. 2007, 69, 347-672.
- (2007) Org. React , vol.69 , pp. 347-672
- Baudoux, J.¹ Cahard, D.²

8
- 85178394634
- (a) Balz, G.; Schiemann, G. Ber. Deutsch. Chem. Ges. 1927, 60, 1186-1190.
- (1927) Ber. Deutsch. Chem. Ges , vol.60 , pp. 1186-1190
- Balz, G.¹ Schiemann, G.²

9
- 67649568446
- (b) Adams, D. J.; Clark, J. H. Chem. Soc. Rev. 1999, 28, 225231.
- (1999) Chem. Soc. Rev , vol.28 , pp. 225231
- Adams, D.J.¹ Clark, J.H.²

10
- 33846175344
- (c) Sandford, G. J. Fluorine Chem. 2007, 128, 90-104.
- (2007) J. Fluorine Chem , vol.128 , pp. 90-104
- Sandford, G.¹

11
- 0003529785
- Marcel Dekker: New York
- Silverman, G. S.; Rakita, P. E. Handbook of Grignard Reagents; Marcel Dekker: New York, 1996.
- (1996) Handbook of Grignard Reagents
- Silverman, G.S.¹ Rakita, P.E.²

12
- 0001421078
- (a) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452-454.
- (1984) J. Am. Chem. Soc , vol.106 , pp. 452-454
- Barnette, W.E.¹

13
- 0025883038
- (b) Differding, E.; Wehrli, M. Tetrahedron Lett. 1991, 32, 3819-3822.
- (1991) Tetrahedron Lett , vol.32 , pp. 3819-3822
- Differding, E.¹ Wehrli, M.²

14
- 33744928374
- (a) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134-7135.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 7134-7135
- Hull, K.L.¹ Anani, W.Q.² Sanford, M.S.³

15
- 67650332711
- (b) Wang, X.; Mei, T.-S.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 7520-7521.
- (2009) J. Am. Chem. Soc , vol.131 , pp. 7520-7521
- Wang, X.¹ Mei, T.-S.² Yu, J.Q.³

16
- 51449084463
- Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993-5996.
- (2008) Angew. Chem., Int. Ed , vol.47 , pp. 5993-5996
- Furuya, T.¹ Kaiser, H.M.² Ritter, T.³

17
- 48749095255
- Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 1006010061. For other electrophilic fluorination reactions from arylpalladium complexes, see:
- (a) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 1006010061. For other electrophilic fluorination reactions from arylpalladium complexes, see:

18
- 38749098194
- (b) Kaspi, A. W.; Yahav-Levi, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2008, 47, 5-7.
- (2008) Inorg. Chem , vol.47 , pp. 5-7
- Kaspi, A.W.¹ Yahav-Levi, A.² Goldberg, I.³ Vigalok, A.⁴

19
- 67749111679
- (c) Ball, N. D.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 3796-3797.
- (2009) J. Am. Chem. Soc , vol.131 , pp. 3796-3797
- Ball, N.D.¹ Sanford, M.S.²

20
- 67749097780
- Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662-1663.
- (2009) J. Am. Chem. Soc , vol.131 , pp. 1662-1663
- Furuya, T.¹ Strom, A.E.² Ritter, T.³

21
- 84889494843
- Boronic acids
- Wiley-VCH: Weinheim
- Hall, D. G. Boronic acids. Preparation and applications in organic synthesis and medicine; Wiley-VCH: Weinheim, 2005.
- (2005) Preparation and applications in organic synthesis and medicine
- Hall, D.G.¹

22
- 0033754675
- For examples, see
- (a) For examples, see: Manickam, G.; Schlüter, A. D. Eur. J. Org. Chem. 2000, 3475-3481.
- (2000) Eur. J. Org. Chem , pp. 3475-3481
- Manickam, G.¹ Schlüter, A.D.²

23
- 0024464543
- (b) Yamamoto, Y.; Seko, T; Němoto, H. J. Org. Chem. 1989, 54, 4734-4736.
- (1989) J. Org. Chem , vol.54 , pp. 4734-4736
- Yamamoto, Y.¹ Seko, T.² Němoto, H.³

24
- 84869312180
- 19F NMR, but its instability and low solubility prevented further characterization. To establish transmetalation and the purity of the resulting arylsilver complex, we also prepared previously characterized 2,4,6-trimethylphenylsilver tetramer, which participated in fluorination under the same reaction conditions as 2 (see Supporting Information for details). For characterization of 2,4,6-trimethylphenysilver tetramer, see:
- 19F NMR, but its instability and low solubility prevented further characterization. To establish transmetalation and the purity of the resulting arylsilver complex, we also prepared previously characterized 2,4,6-trimethylphenylsilver tetramer, which participated in fluorination under the same reaction conditions as 2 (see Supporting Information for details). For characterization of 2,4,6-trimethylphenysilver tetramer, see:

25
- 0000727781
- (b) Meyer, E. M.; Gambarotta, S.; Floriani, C.; Chiesi-Villa, A.; Guastini, C Organometallics 1989, 8, 1067-1079.
- (1989) Organometallics , vol.8 , pp. 1067-1079
- Meyer, E.M.¹ Gambarotta, S.² Floriani, C.³ Chiesi-Villa, A.⁴ Guastini, C.⁵

26
- 67649565092
- Byproducts resulting from C-H instead of C-F bond formation, as found for the Ag-mediated fluorination of arylstannanes, were not observed in the fluorination of boronic acids reported here. C-H bond formation in the Ag-mediated fluorination of arylstannanes is not due to the presence of water and cannot be suppressed by the addition of molecular sieves. We have determined that Bu3SnOTf is involved in C-H bond formation. Transmetalation from arylboronic acids to Ag in methanol produces B(OMe)3, which does not provoke C-H bond formation
- 3, which does not provoke C-H bond formation.

27
- 0026588144
- Tius, M. A.; Kawakami, J. K. Synth Commun. 1992, 22, 14611471.
- (a) Tius, M. A.; Kawakami, J. K. Synth Commun. 1992, 22, 14611471.

28
- 0002565898
- (b) Tius, M. A.; Kawakami, J. K. Synlett. 1993, 207-208.
- (1993) Synlett , pp. 207-208
- Tius, M.A.¹ Kawakami, J.K.²

29
- 0028945863
- (c) Tius, M. A.; Kawakami, J. K. Tetrahedron 1995, 51, 3997-4010.
- (1995) Tetrahedron , vol.51 , pp. 3997-4010
- Tius, M.A.¹ Kawakami, J.K.²

30
- 0035819654
- Greedy, B.; Gourverneur, V. Chem. Commun. 2001, 233-234.
- (2001) Chem. Commun , pp. 233-234
- Greedy, B.¹ Gourverneur, V.²

31
- 0000213491
- Petasis, N. A.; Yudin, A. K.; Zavialov, I. A.; Prakash, G. K. S.; Olah, G. A. Synlett. 1997, 606-608.
- (1997) Synlett , pp. 606-608
- Petasis, N.A.¹ Yudin, A.K.² Zavialov, I.A.³ Prakash, G.K.S.⁴ Olah, G.A.⁵

32
- 0033603859
- (a) Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 1999, 121, 7696-7697.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 7696-7697
- Iverson, C.N.¹ Smith, M.R.²

33
- 0035818034
- (b) Tse, M. K.; Cho, J.-Y.; Smith, M. R. Org. Lett. 2001, 3, 2831-2833.
- (2001) Org. Lett , vol.3 , pp. 2831-2833
- Tse, M.K.¹ Cho, J.-Y.² Smith, M.R.³

34
- 0037160365
- (c) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390-391.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 390-391
- Ishiyama, T.¹ Takagi, J.² Ishida, K.³ Miyaura, N.⁴ Anastasi, N.R.⁵ Hartwig, J.F.⁶

35
- 0037059546
- (d) Cho, J.Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305-308.
- (2002) Science , vol.295 , pp. 305-308
- Cho, J.Y.¹ Tse, M.K.² Holmes, D.³ Maleczka, R.E.⁴ Smith, M.R.⁵

36
- 33947118185
- (e) Murphy, J. M.; Tzschucke, C. C.; Hartwig, J. F. Org. Lett. 2007, 9, 757-760.
- (2007) Org. Lett , vol.9 , pp. 757-760
- Murphy, J.M.¹ Tzschucke, C.C.² Hartwig, J.F.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.