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Volumn 34, Issue 33, 1993, Pages 5265-5268

Palladium catalyzed coupling reactions of 2,3-dihydrofuran using high pressure conditions

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0027301643 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)73969-4 Document Type: Article

Times cited : (39)

References (21)

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5
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- R. Noyori, Tokyo Kagaku Dozin, Co., Ltd, Tokyo
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- Hayashi¹

6
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- Ozawa¹ Kubo² Hayashi³

7
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- Catalytic asymmetric arylation of 2,3-dihydrofuran with aryl triflates
- (1991) Journal of the American Chemical Society , vol.113 , pp. 1419-1421
- Ozawa¹ Kubo² Hayashi³

8
- 1542540752
- Reaktionsdynamik in der Chemie von Koordinationsverbindungen - Anwendung von Hochdruck-Techniken
- For excellent reviews on coordination chemistry under high pressure conditions see
- (1986) Angewandte Chemie , vol.98 , pp. 671-680
- Eldik¹

9
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- Understanding Reaction Dynamics in Coordination Chemistry—Application of High Pressure Techniques
- (1986) Angewandte Chemie International Edition in English , vol.25 , pp. 673
- v¹

11
- 0001324836
- Inter- and intramolecular hetero diels-alder reactions, 40. Effect of high pressure on the stereoselectivity of intermolecular hetero diels-alder reactions
- Leading references on pressure induced selectivity
- (1992) Chemische Berichte , vol.125 , pp. 2249-2258
- Tietze¹ Hübsch² Oelze³ Ott⁴ Tost⁵ Wörner⁶ Buback⁷

12
- 0000472096
- Inter- and Intramolecular Hetero Diels-Alder Reactions, Part XXVI. Diastereoselectivity and Kinetics of Intermolecular Hetero Diels-Alder Reactions under High Pressure. A Significant Pressure-Induced Increase in Stereoselectivity
- (1989) Chemische Berichte , vol.122 , pp. 1179-1186
- Buback¹ Tost² Hübsch³ Voß⁴ Tietze⁵

14
- 84918741447
- 2 (6.7 mg, 30 μmol), triphenylphosphine (31 mg, 120 μmol), and diisopropylethylamine (380 mg, 3.0 mmol) in 15 ml THF / acetonitrile (1:1) were stirred at r.t. for 20 min. Subsequently, to 1.5 ml of this catalyst solution a solution of iodobenzene (2-I) (20 mg, 0.1 mmol) and 2,3-dihydrofuran (1) (35 mg, 0.5 mmol) in 500 μl THF / acetonitrile (1:1) were added. The solution was divided into two equal volumes, one part was heated at 60°C for 70 h at normal pressure, the other part was sealed in a Teflon tube and heated at 60°C for 70 h at a pressure of 10 kbar. The mixtures were filtrated on 0.5 g silica gel (ether) and analyzed by capillary GC.

15
- 84918717355
- The procedure given in Note 6 has been scaled up by a factor of 50 (in 20 ml solvent) for selected cases leading to identical results.

16
- 84918743494
- At normal pressure 3 can only be selectively formed by the addition of 2 equivalents of silver salts: cf. Ref. 2.

17
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- Organic Synthesis under High Pressure; I
- (1985) Synthesis , pp. 1-26
- Matsumoto¹ Sera² Uchida³

18
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- Activation and reaction volumes in solution. 2
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- v¹ Asano² le³

19
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- (R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl
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- Takaya¹ Mashima² Koyano³ Yagi⁴ Kumobayashi⁵ Taketomi⁶ Akutagawa⁷ Noyori⁸

20
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- The enantiomeric excess was determined by GC using a 6-methyl-2,3-pentyl-β-cyclodextrine column.

21
- 84918727180
- Procedure cf. Ref. 5: Instead of triphenylphosphine (R)-BINAP (3.7 mg, 6 μmol) and instead of 2-I 2-ONf (39 mg, 0.1 mmol) were used.

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