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Volumn 10, Issue 2, 2008, Pages 289-292

(BDP)CuH: A "hot" Stryker's reagent for use in achiral conjugate reductions

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EID: 38749131256 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol702689v Document Type: Article

Times cited : (131)

References (19)

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- (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
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- Mahoney, W.S.¹ Brestensky, D.M.² Stryker, J.M.³

2
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- (b) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
- (1989) J. Am. Chem. Soc , vol.111 , pp. 8818
- Mahoney, W.S.¹ Stryker, J.M.²

3
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- (a) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627.
- (1998) Tetrahedron Lett , vol.39 , pp. 4627
- Lipshutz, B.H.¹ Keith, J.² Papa, P.³ Vivian, R.⁴

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- (b) Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 9473
- Appella, D.H.¹ Moritani, Y.² Shintani, R.³ Ferreira, E.M.⁴ Buchwald, S.L.⁵

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- (2003) Angew. Chem., Int. Ed , vol.42 , pp. 4793
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- (e) Desrosiers, J.-N.; Charette, A. Angew. Chem., Int. Ed. 2007, 46, 5955.
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8
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- Brestensky, D. M.; Huseland, D. E.; McGettigan, C.; Stryker, J. M. Tetrahedron Lett. 1988, 29, 3749.
- (1988) Tetrahedron Lett , vol.29 , pp. 3749
- Brestensky, D.M.¹ Huseland, D.E.² McGettigan, C.³ Stryker, J.M.⁴

9
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- Miao, R.; Li, S.; Chiu, P. Tetrahedron 2007, 63, 6737.
- (2007) Tetrahedron , vol.63 , pp. 6737
- Miao, R.¹ Li, S.² Chiu, P.³

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- Lipshutz, B. H.; Papa, P. Angew. Chem., Int. Ed. 2002, 41, 4580.
- (2002) Angew. Chem., Int. Ed , vol.41 , pp. 4580
- Lipshutz, B.H.¹ Papa, P.²

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13
- 38749099721
- 3 to (BDP)CuH leads to no change in the spectrum for the hydride signal at δ 1.49.
- 3 to (BDP)CuH leads to no change in the spectrum for the hydride signal at δ 1.49.

14
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- (a) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417.
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17
- 38749104594
- 2O (20.0 mg, 0.1 mmol), bis-diphenylphoshinobenzene (4.46 mg, 0.01 mmol), and triphenylphosphine (27.0 mg, 0.1 mmol). The reagents were dissolved in freshly distilled toluene (8.0 mL) and allowed to stir at room temperature for 1 h. Polymethylhydrosiloxane (PMHS) (2.0 mL, 30 mmol) was added dropwise to the stirring solution. There was an immediate color change from blue to red. The stock solution was thoroughly purged with argon and sealed. Storage in a refrigerator is recommended.
- 2O (20.0 mg, 0.1 mmol), bis-diphenylphoshinobenzene (4.46 mg, 0.01 mmol), and triphenylphosphine (27.0 mg, 0.1 mmol). The reagents were dissolved in freshly distilled toluene (8.0 mL) and allowed to stir at room temperature for 1 h. Polymethylhydrosiloxane (PMHS) (2.0 mL, 30 mmol) was added dropwise to the stirring solution. There was an immediate color change from blue to red. The stock solution was thoroughly purged with argon and sealed. Storage in a refrigerator is recommended.

18
- 0000919121
- Preparation of 1,2-Bis(diphenylphosphino)benzene. A flame-dried 250 mL round-bottom flask cooled under argon was charged with freshly distilled THF (75 mL, Potassium (3.52 g, 90.0 mmol) was added in small pieces with stirring. The reaction flask was fitted with a reflux condenser under positive argon pressure, and chlorodiphenylphosphine (8 mL, 45.0 mmol) was added dropwise. The solution was then heated to reflux until potassium was consumed and the mixture had assumed a characteristic red color. To this refluxing solution was added o-difluorobenzene (2 mL, 20.0 mmol) via syringe followed by freshly distilled toluene (100 mL, The solution was refluxed for 24 h and then cooled to rt, and the volatiles were removed by rotary evaporation. The solution was redissolved in toluene, and 5 g of activated charcoal (Norit A) was added. The resulting mixture was hot filtered through a Celite pad and concentrated in vacuo, and the residue was recrystallized from toluene yielding 1
- 12b mp 183-185°C). (b) McFarlane, H. C. E. Polyhedron 1983, 2, 303.

19
- 38749087144
- Based on prices quoted in the latest Sigma-Aldrich catalog, costs to reduce 1 mol of substrate employing (a) stoichiometric Stryker's reagent (SR) = $18,000; (b) using 5 mol % SR = $600. The same scale reduction using (BDP)CuH (0.1 mol %) would cost $20.
- Based on prices quoted in the latest Sigma-Aldrich catalog, costs to reduce 1 mol of substrate employing (a) stoichiometric Stryker's reagent (SR) = $18,000; (b) using 5 mol % SR = $600. The same scale reduction using (BDP)CuH (0.1 mol %) would cost $20.

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