SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 2, 2009, Pages 225-228

Palladium(0)-catalyzed benzylation of H-phosphonate diesters: An efficient entry to benzylphosphonates

(2) Lavén, Gaston a Stawinski, Jacek a,b

a STOCKHOLM UNIVERSITY (Sweden)

b INSTITUTE OF BIOORGANIC CHEMISTRY (Poland)

Author keywords

Benzylphosphonates; C phosphonates; H phosphonates; Palladium cross coupling

Indexed keywords

EID: 62349095379 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087522 Document Type: Article

Times cited : (38)

References (48)

1
- 0014663311
- (a) Kittredge, J. S.; Roberts, E. Science 1969, 164, 37.
- (1969) Science , vol.164 , pp. 37
- Kittredge, J.S.¹ Roberts, E.²

2
- 35848942616
- (b) White, A. K.; Metcalf, W. W. Annu. Rev. Microbiol. 2007, 61, 379.
- (2007) Annu. Rev. Microbiol , vol.61 , pp. 379
- White, A.K.¹ Metcalf, W.W.²

3
- 1542690351
- Engel, R. Chem. Rev. 1977, 77, 349.
- (1977) Chem. Rev , vol.77 , pp. 349
- Engel, R.¹

4
- 84913150907
- Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon 1991, 63, 193.
- (1991) Phosphorus, Sulfur Silicon , vol.63 , pp. 193
- Kafarski, P.¹ Lejczak, B.²

5
- 0034499290
- Huang, J. M.; Chen, R. Y. Heteroatom. Chem. 2000, 11, 480.
- (2000) Heteroatom. Chem , vol.11 , pp. 480
- Huang, J.M.¹ Chen, R.Y.²

6
- 0003858185
- Engel, R, Ed, Marcel Dekker: New York
- Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; Marcel Dekker: New York, 1992, 559.
- (1992) Handbook of Organophosphorus Chemistry , pp. 559
- Engel, R.¹

7
- 37849036602
- (a) Michaelis, A.; Kaehne, R. Chem. Ber. 1898, 31, 1048.
- (1898) Chem. Ber , vol.31 , pp. 1048
- Michaelis, A.¹ Kaehne, R.²

8
- 4243404632
- Houben-Weyl, Müller, E, Ed, George Thieme Verlag: Stuttgart
- (b) Methoden der organischen Chemie (Houben-Weyl), Vol. XII/1; Müller, E., Ed.; George Thieme Verlag: Stuttgart, 1964, 433.
- (1964) Methoden der organischen Chemie , vol.XII 1 , pp. 433

9
- 33845557502
- Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
- (1981) Chem. Rev , vol.81 , pp. 415
- Bhattacharya, A.K.¹ Thyagarajan, G.²

10
- 0000578250
- (a) Michaelis, A.; Becker, T. Chem. Ber. 1897, 30, 1003.
- (1897) Chem. Ber , vol.30 , pp. 1003
- Michaelis, A.¹ Becker, T.²

11
- 62349088314
- Houben-Weyl, Müller, E, Ed, George Thieme Verlag: Stuttgart
- (b) Methoden der organischen Chemie (Houben-Weyl), Vol. XII/1; Müller, E., Ed.; George Thieme Verlag: Stuttgart, 1964, 446.
- (1964) Methoden der organischen Chemie , vol.XII 1 , pp. 446

12
- 0030845073
- (c) Waschbüsch, R.; Carran, J.; Marinetti, A.; Savignac, P. Synthesis 1997, 727.
- (1997) Synthesis , pp. 727
- Waschbüsch, R.¹ Carran, J.² Marinetti, A.³ Savignac, P.⁴

13
- 33845471003
- Brill, T. B.; Landon, S. J. Chem. Rev. 1984, 84, 577.
- (1984) Chem. Rev , vol.84 , pp. 577
- Brill, T.B.¹ Landon, S.J.²

14
- 8344227723
- Harizi, A.; Zantour, H. Phosphorus, Sulfur Silicon 2004, 179, 1883.
- (2004) Phosphorus, Sulfur Silicon , vol.179 , pp. 1883
- Harizi, A.¹ Zantour, H.²

15
- 84987263034
- Saady, M.; Lebeau, L.; Mioskowski, C. Helv. Chim. Acta 1995, 78, 670.
- (1995) Helv. Chim. Acta , vol.78 , pp. 670
- Saady, M.¹ Lebeau, L.² Mioskowski, C.³

16
- 0442284727
- DeBruin, K. E.; Chandrasekaran, S. J. Am. Chem. Soc. 1973, 95, 974.
- (1973) J. Am. Chem. Soc , vol.95 , pp. 974
- DeBruin, K.E.¹ Chandrasekaran, S.²

17
- 0343052544
- Kers, A.; Stawinski, J.; Dembkowski, L.; Kraszewski, A. Tetrahedron 1997, 53, 12691.
- (1997) Tetrahedron , vol.53 , pp. 12691
- Kers, A.¹ Stawinski, J.² Dembkowski, L.³ Kraszewski, A.⁴

18
- 0040338527
- (a) Witt, D.; Rachon, J. Phosphorus, Sulfur Silicon 1995, 107, 33.
- (1995) Phosphorus, Sulfur Silicon , vol.107 , pp. 33
- Witt, D.¹ Rachon, J.²

19
- 0001762469
- (b) Witt, D.; Rachon, J. Heteroatom. Chem. 1996, 7, 359.
- (1996) Heteroatom. Chem , vol.7 , pp. 359
- Witt, D.¹ Rachon, J.²

20
- 85163173615
- (a) Birckenbach, L.; Kellermann, K. Chem. Ber. 1925, 58, 786.
- (1925) Chem. Ber , vol.58 , pp. 786
- Birckenbach, L.¹ Kellermann, K.²

21
- 84943879463
- (b) Michalski, J.; Skowronska, A.; Lopusinski, A. Phosphorus, Sulfur Silicon 1991, 58, 61.
- (1991) Phosphorus, Sulfur Silicon , vol.58 , pp. 61
- Michalski, J.¹ Skowronska, A.² Lopusinski, A.³

22
- 0033461799
- (a) Yao, Z.-J.; Gao, Y.; Burke, T. R. Tetrahedron: Asymmetry 1997, 10, 3727.
- (1997) Tetrahedron: Asymmetry , vol.10 , pp. 3727
- Yao, Z.-J.¹ Gao, Y.² Burke, T.R.³

23
- 0141786894
- (b) Li, P.; Zhang, M.; Peach, M. L.; Liu, H.; Yang, D.; Roller, P. P. Org. Lett. 2003, 5, 3095.
- (2003) Org. Lett , vol.5 , pp. 3095
- Li, P.¹ Zhang, M.² Peach, M.L.³ Liu, H.⁴ Yang, D.⁵ Roller, P.P.⁶

24
- 0024993157
- Löschner, T.; Engels, J. W. Nucleic Acids Res. 1990, 18, 5083.
- (1990) Nucleic Acids Res , vol.18 , pp. 5083
- Löschner, T.¹ Engels, J.W.²

25
- 0032882628
- (a) Alt, M.; Eisenhardt, S.; Serwe, M.; Renz, R.; Engels, J. W.; Caselmann, W. H. Eur. J. Clin. Invest. 1999, 29, 868.
- (1999) Eur. J. Clin. Invest , vol.29 , pp. 868
- Alt, M.¹ Eisenhardt, S.² Serwe, M.³ Renz, R.⁴ Engels, J.W.⁵ Caselmann, W.H.⁶

26
- 0034944358
- (b) Lehman, T. J.; Engels, J. W. Bioorg. Med. Chem. 2001, 9, 1827.
- (2001) Bioorg. Med. Chem , vol.9 , pp. 1827
- Lehman, T.J.¹ Engels, J.W.²

27
- 0036377059
- Amberg, S.; Engels, J. W. Helv. Chim. Acta 2002, 85, 2503.
- (2002) Helv. Chim. Acta , vol.85 , pp. 2503
- Amberg, S.¹ Engels, J.W.²

28
- 0035930659
- Johansson, T.; Stawinski, J. Chem. Commun. 2001, 2564.
- (2001) Chem. Commun , pp. 2564
- Johansson, T.¹ Stawinski, J.²

29
- 36749010105
- Lavén, G.; Stawinski, J. Coll. Symposium Series 2005, 7, 195.
- (2005) Coll. Symposium Series , vol.7 , pp. 195
- Lavén, G.¹ Stawinski, J.²

30
- 0032814027
- Abbas, S.; Hayes, C. J. Synlett 1999, 1124.
- (1999) Synlett , pp. 1124
- Abbas, S.¹ Hayes, C.J.²

31
- 0000664890
- Fitton, P.; McKeon, J. E.; Ream, B. C. J. Chem. Soc., Chem. Commun. 1969, 370.
- (1969) J. Chem. Soc., Chem. Commun , pp. 370
- Fitton, P.¹ McKeon, J.E.² Ream, B.C.³

32
- 38349128181
- Liegault, B.; Renaud, J.-L.; Bruneau, C. Chem. Soc. Rev. 2008, 36, 290.
- (2008) Chem. Soc. Rev , vol.36 , pp. 290
- Liegault, B.¹ Renaud, J.-L.² Bruneau, C.³

33
- 0037060980
- Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
- (2002) Tetrahedron , vol.58 , pp. 2041
- Prim, D.¹ Campagne, J.-M.² Joseph, D.³ Andrioletti, B.⁴

34
- 20444436468
- Bravo-Altamirano, K.; Huang, Z. H.; Montchamp, J. L. Tetrahedron 2005, 61, 6315.
- (2005) Tetrahedron , vol.61 , pp. 6315
- Bravo-Altamirano, K.¹ Huang, Z.H.² Montchamp, J.L.³

35
- 2642544664
- Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218.
- (2004) Chem. Soc. Rev , vol.33 , pp. 218
- Schwan, A.L.¹

36
- 0034701604
- Abbas, S.; Hayes, C. J.; Worden, S. Tetrahedron Lett. 2000, 41, 3215.
- (2000) Tetrahedron Lett , vol.41 , pp. 3215
- Abbas, S.¹ Hayes, C.J.² Worden, S.³

37
- 62349133919
- Presence of water in the reaction mixture facilitated reduction of palladium(II) acetate and resulted in improved reproducibility of the reactions
- Presence of water in the reaction mixture facilitated reduction of palladium(II) acetate and resulted in improved reproducibility of the reactions.

38
- 1542286006
- Stockland, R. A.; Levine, A. M.; Giovine, M. T.; Guzei, I. A.; Cannistra, J. C. Organometallics 2004, 23, 647.
- (2004) Organometallics , vol.23 , pp. 647
- Stockland, R.A.¹ Levine, A.M.² Giovine, M.T.³ Guzei, I.A.⁴ Cannistra, J.C.⁵

39
- 30344477372
- Klingensmith, L. M.; Strieter, E. R.; Barder, T. E.; Buchwald, S. L. Organometallics 2006, 25, 82.
- (2006) Organometallics , vol.25 , pp. 82
- Klingensmith, L.M.¹ Strieter, E.R.² Barder, T.E.³ Buchwald, S.L.⁴

40
- 62349137847
- Lower yields of diphenyl benzylphosphonate for the reactions of diphenyl H-phosphonate (Table 2, entries 9 and 10) were due to partial hydrolysis of the starting H-phosphonate under the reaction conditions.
- Lower yields of diphenyl benzylphosphonate for the reactions of diphenyl H-phosphonate (Table 2, entries 9 and 10) were due to partial hydrolysis of the starting H-phosphonate under the reaction conditions.

41
- 36749062348
- Kalek, M.; Stawinski, J. Organometallics 2007, 26, 5840.
- (2007) Organometallics , vol.26 , pp. 5840
- Kalek, M.¹ Stawinski, J.²

42
- 33847088632
- Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434.
- (1977) Acc. Chem. Res , vol.10 , pp. 434
- Stille, J.K.¹ Lau, K.S.Y.²

43
- 0000407644
- Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
- (1999) J. Organomet. Chem , vol.576 , pp. 254
- Amatore, C.¹ Jutand, A.²

44
- 0000037108
- Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
- (1998) Acc. Chem. Res , vol.31 , pp. 852
- Hartwig, J.F.¹

45
- 0026645156
- Stawinski, J.; Strömberg, R.; Zain, R. Tetrahedron Lett. 1992, 33, 3185.
- (1992) Tetrahedron Lett , vol.33 , pp. 3185
- Stawinski, J.¹ Strömberg, R.² Zain, R.³

46
- 62349139016
- Typical Procedure for the Preparation of Dinucleoside Benzylphosphonates 2: Pd(OAc)2 (0.05 mmol, Xantphos (0.1 mmol, and N,N-diisopropylethylamine (mmol, were refluxed for ca. 3 h in degassed THF (5 mL) containing H2O (0.025 mmol, To this, separate diastereomers of dinucleoside H-phosphonate 1 (1a or 1b; 0.5 mmol),37 and benzyl bromide (0.75 mmol, dissolved in THF (2 mL, were added and the mixture was heated under reflux for 3 h. After concentration and partition of the reaction mixture between sat. aq NaHCO3 and CH2Cl2, the product was purified by silica gel column chromatography using a stepwise gradient of ethanol (0-5, in CH 2Cl2 containing triethylamine (0.02, Compounds 2 were obtained as off-white solids (purity >98, 1H NMR spectroscopy, Compound 2a: 83% yield from 1a probably RP diastereomer
- 31P NMR spectroscopy.

47
- 37049087486
- (a) Xu, Y.; Zhang, J. J. Chem. Soc., Chem. Commun. 1986, 1606.
- (1986) J. Chem. Soc., Chem. Commun , pp. 1606
- Xu, Y.¹ Zhang, J.²

48
- 0008558831
- (b) Zhang, J.; Xu, Y.; Huang, G.; Guo, H. Tetrahedron Lett. 1988, 29, 1955.
- (1988) Tetrahedron Lett , vol.29 , pp. 1955
- Zhang, J.¹ Xu, Y.² Huang, G.³ Guo, H.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.