SCOPUS 정보 검색 플랫폼

Tetrahedron Letters

Volumn 44, Issue 47, 2003, Pages 8617-8621

Mild and efficient Cs2CO3-promoted synthesis of phosphonates

(4) Cohen, Richard J a Fox, Daniel L a Eubank, Jarrod F a Salvatore, Ralph Nicholas a

a WESTERN KENTUCKY UNIVERSITY (United States)

Author keywords

Cesium carbonate; Dialkyl phosphite; Phosphonate; Tetrabutylammonium iodide

Indexed keywords

ALKYL GROUP; CESIUM; HALIDE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; BIODIVERSITY; CHEMICAL REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 0142199988 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/j.tetlet.2003.09.045 Document Type: Article

Times cited : (68)

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- 4) (0.50 g, 0.42 mL, 4.54 mmol, 1 equiv.) in anhydrous DMF (23 mL) was added cesium carbonate (4.44 g, 13.6 mmol, 3 equiv.) and tetrabutylammonium iodide (5.03 g, 13.6 mmol, 3 equiv.) with vigorous stirring for 1 hour at room temperature under a nitrogen atmosphere. After this time period, benzyl chloride (1.73 g, 1.6 mL, 13.6 mmol, 3 equiv.) was added and stirred for an additional 24 h. The resulting milky white suspension was then poured into water (30 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (2×30 mL), brine (30 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo, and subjected to flash chromatography (hexanes-EtOAc, 9:1 v/v) affording dimethyl benzylphosphonate (5) as a clear yellow oil (0.88 g, 97%).
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39
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- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
- (2001) Tetrahedron Lett. , vol.42 , pp. 2055
- Salvatore, R.N.¹ Sahab, S.² Jung, K.W.³

40
- 0034627338
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
- (2000) Tetrahedron Lett. , vol.41 , pp. 9705
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41
- 0035959472
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
- (2001) Tetrahedron Lett. , vol.42 , pp. 6023
- Salvatore, R.N.¹ Ledger, J.A.² Jung, K.W.³

42
- 0033603624
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
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43
- 0037156592
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
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44
- 0035804470
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
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- Salvatore, R.N.¹ Shin, S.I.² Flanders, V.L.³ Jung, K.W.⁴

45
- 0037039904
- For examples of efficient cesium-promoted alkylations, see: (a) Parrish, J. P.; Dueno, E. E.; Kim, S.-I.; Jung, K. W. Synth. Commun. 2000, 30, 2687; (b) Salvatore, R. N.; Flanders, V. L.; Ha, D.; Jung, K. W. Org. Lett. 2000, 2, 2797; (c) Dueno, E. E.; Chu, F.; Kim, S.-I.; Jung, K. W. Tetrahedron Lett. 1999, 40, 1843; (d) Salvatore, R. N.; Nagle, A. S.; Schmidt, S. E.; Jung, K. W. Org. Lett. 1999, 1, 1893; (e) Salvatore, R. N.; Shin, S. I.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2001, 66, 1035; (f) Salvatore, R. N.; Sahab, S.; Jung, K. W. Tetrahedron Lett. 2001, 42, 2055; (g) Salvatore, R. N.; Schmidt, S. E.; Shin, S. I.; Nagle, A. S.; Worrell, J. H.; Jung, K. W. Tetrahedron Lett. 2000, 41, 9705; (h) Salvatore, R. N.; Ledger, J. A.; Jung, K. W. Tetrahedron Lett. 2001, 42, 6023; (i) Kim, S.-I.; Chu, F.; Dueno, E. E.; Jung, K. W. J. Org. Chem. 1999, 64, 4578; (j) Salvatore, R. N.; Chu, F.; Nagle, A. S.; Kapxhiu, E. A.; Cross, R. M.; Jung, K. W. Tetrahedron 2002, 58, 3329; (k) Salvatore, R. N.; Shin, S. I.; Flanders, V. L.; Jung, K. W. Tetrahedron Lett. 2001, 42, 1799; (l) Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674.
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- Salvatore, R.N.¹ Nagle, A.S.² Jung, K.W.³

46
- 0142255976
- TBAI is strongly believed to act as a phase-transfer catalyst facilitating alkylations and higher product yields. For other phase-transfer catalyzed P-alkylations, see: (a) Kem, K. M.; Nguyen, N. V.; Cross, D. J. J. Org. Chem. 1981, 46, 5188; (b) Weber, W. P.; Gokel, G. W. Phase Transfer Catalysts in Organic Synthesis; Springer-Verlag: New York, 1977; (c) Starks, C. M.; Liotta, C. Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978; (d) Fedorynski, M.; Wojciechowski, K.; Matacz, Z.; Makosza, M. J. Org. Chem. 1978, 43, 4682; (e) Kluba, M.; Zwierzak, A. Synthesis 1978, 2, 134-137.
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47
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- Springer-Verlag: New York
- TBAI is strongly believed to act as a phase-transfer catalyst facilitating alkylations and higher product yields. For other phase-transfer catalyzed P-alkylations, see: (a) Kem, K. M.; Nguyen, N. V.; Cross, D. J. J. Org. Chem. 1981, 46, 5188; (b) Weber, W. P.; Gokel, G. W. Phase Transfer Catalysts in Organic Synthesis; Springer-Verlag: New York, 1977; (c) Starks, C. M.; Liotta, C. Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978; (d) Fedorynski, M.; Wojciechowski, K.; Matacz, Z.; Makosza, M. J. Org. Chem. 1978, 43, 4682; (e) Kluba, M.; Zwierzak, A. Synthesis 1978, 2, 134-137.
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48
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49
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- TBAI is strongly believed to act as a phase-transfer catalyst facilitating alkylations and higher product yields. For other phase-transfer catalyzed P-alkylations, see: (a) Kem, K. M.; Nguyen, N. V.; Cross, D. J. J. Org. Chem. 1981, 46, 5188; (b) Weber, W. P.; Gokel, G. W. Phase Transfer Catalysts in Organic Synthesis; Springer-Verlag: New York, 1977; (c) Starks, C. M.; Liotta, C. Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978; (d) Fedorynski, M.; Wojciechowski, K.; Matacz, Z.; Makosza, M. J. Org. Chem. 1978, 43, 4682; (e) Kluba, M.; Zwierzak, A. Synthesis 1978, 2, 134-137.
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50
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- In most examples, the starting dialkyl phosphites were not completely consumed during the reaction, accounting for additional mass balance.

52
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- 13C, and 2D NMR analyses indicate the product as a single diastereomer.

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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.