Silicon-based cross-coupling reagent and production method...

Details Silicon-based cross-coupling reagent and production method... Silicon-based cross-coupling reagent and production method...

2011-06-14

2011-06-14

Solola, Taofiq A (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07960571

ABSTRACT:
In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.

REFERENCES:
patent: 04-283521 (1992-10-01), None
patent: 08-310972 (1996-11-01), None
Gschwend et al., Org. Reactions, (1979), vol. 26.
Rabideau et al., Org. Reactions, (1992), vol. 42.
Fleming et al., Org. Reactions, (1989), vol. 37.
Rickborn, Org. Reactions, (1998), vol. 53;.
Beck, e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Comins et al., e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Campbell et al., e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Mathieu-Pelta, et al., e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Sorgi, et al., e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Ovaska, e-EROS Encyclopedia of Reagents for Org. Synthes. (2001).
Haruhiko Taguchi et al. “Copper(I)tert-butoxide-promoted coupling ofo-(1-hydroxyalkyl)arylsilanes with organic halides.” Tetrahedron Letters 45, 2004, pp. 429-432.
Scott E. Denmark et al. “Organosilicon Compounds in Cross-Coupling Reactions.” Metal Catalyzed Cross-Coupling Reactions, 2ndEdition, 2004 Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim, pp. 163-216.
Kenichiro ITAMI et al. “A General and Straightforward Route toward Diarylmethanes. Integrated Cross-Coupling Reactions Using (2-Pyridyl)silylmethylstannane as an Air-Stable, Storable, and Versatile Coupling Platform.” Organic Letters 2002, vol. 4, No. 21, Sep. 19, 2002, pp. 3635-3638.
James C. Anderson et al. “Vinyldimethylphenylsilanes as Safety Catch Silanols in Fluoride-Free Palladium-Catalyzed Cross-Coupling Reactions.” J. Org. Chem. 2004, Nov. 9, 2004, pp. 8971-8974.
Emiko Hagiwara et al. “NaOH-Promoted Cross-Coupling Reactions of Organosilicon Compounds with Organic Halides: Practical Routes to Biaryls, Alkenylarenes and Conjugated Dienes.” Tetrahedron Letters, vol. 38, No. 3, 1997, pp. 439-442.
Christian Wolf et al. “Palladium-Phosphinous Acid-Catalyzed NaOH-Promoted Cross-Coupling Reactions of Arylsiloxanes with Aryl Chlorides and Bromides in Water.” Organic Letters 2004, vol. 6, No. 7, Mar. 9, 2004, pp. 1147-1150.
Kazunori Hirabayashi et al. “Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) Oxide.” J. Org. Chem. 2000, Jul. 29, 2000, pp. 5342-5349.
Haruhiko Taguchi et al. “Copper(I) tert-Butoxide-Promoted 1,4 Csp2toO Silyl Migration: Generation of Vinyl Copper Equivalents and Their Stereospecific Cross-Coupling with Allylic, Aryl, and Vinylic Halides.” J. Org. Chem. 2002, Nov. 1, 2002, pp. 8450-8456.
Mitsuru Shindo et al. “Intramolecularly Activated Vinylsilanes: Fluoride-Free Cross-Coupling of (Z)-β-(Trialkylsilyl)acrylic Acids.” Synlett 2005, No. 1, pp. 0176-0178.
Akira Hosomi et al. “Pentacoordinate Organosilicon Compounds in Organic Synthesis: Cross-Coupling of Alkenylsiliconates with Organic Halides and Triflates Catalyzed by Palladium Complex.” Chem. Pharm. Bull, 1988, pp. 4622-4625.
W. Michael Seganish et al. “Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Bromides Using Microwave Irradiation.” Organic Letters 2004, vol. 6, No. 23, Oct. 22, 2004, pp. 4379-4381.
Paul F. Hudrlik et al. “Alkoxides ofo-silyl benzyl alcohols in cleavage reactions: approaches to benzyl and silyl anion equivalents.” Can. J. Chem., Oct. 25, 2000, pp. 1421-1427.
Paul F. Hudrlik et al. “Generation of Anionic Intermediates by Intramolecular Nucleophilic Attack at Silicon.” Tetrahedron Letters, vol. 33, No. 45, 1992, pp. 6747-6750.
Yohsuke Yamamoto et al. “Intramolecular Cyclization ofo-Silylbenzyl Alcohols with Elimination of Hydrocarbon Via Hypervalent Silicon Intermediates: Effect of Structure on the Selectivity for Elimination.” Tetrahedron Letters, vol. 30, No. 6, 1989, pp. 725-728.
John W. Fitch et al. “Lithiation and silylation reactions of 1,4-bis(1,1,1,3,3,3-hexafluoro-2-hydroxy-2-propyl) benzene.” Journal of Organometallic Chemistry 522, 1996, pp. 55-57.
Ulrich Wannagat et al. “Beiträge zur Chemie der Silicium-Stickstoffverbindungen.” Journal of Organocmetallic Chemistry, 1988, pp. 95-108. English Abstract.
Shaundra Riggleman et al. “Application of Silicon-Based Cross-Coupling Technology to Triflates.” J. Org. Chem. 2003, Sep. 25, 2003, pp. 8106-8109.
Yousef M. Hijji et al., “Preparation of o-(Silyl) Benzyl Alcohols”, Synthetic Communications, 27 (24), 4297-4308 (1997).
“Silicon-based Cross-Coupling Reaction via Intramolecular Activation”: The Chemical Society of Japan, 85th Spring Meeting 2005, Lecture Proceedings II, p. 909 4 A6-09 (Mar. 11, 2005).
“Fluoride-free Silicon-based Cross-Coupling Reaction via Intramolecular Activation”: The 4th International Symposium of the Kyoto COE Project, Elements Science, p. 122, Jan. 6, 2005.

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