4,4,6-trimethyl-2-[1-(trifluoromethyl)vinyl]-1,3,2-dioxaborinane

4,4,6-trimethyl-2-[1-(trifluoromethyl)vinyl]-1,3,2-dioxaborinane 1-(Trifluoromethyl)vinylboronic acid hexylene glycol ester CAS: 1011460-68-6 MDL: MFCD08669623

Organic Synthesis, Transition Metal Coupling, Organofluorine Chemistry, Pinacol Ester Coupling 

 Selected Reactions:      Pinacol Ester Derivative Coupling Reactions

1.) Palladium(0)-Catalyzed Cross-Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters, Ishiyama, Tatsuo, Murata, Miki, Miyaura, Norio, Journal of Organic Chemistry (1995), 60(23), 7508-10. DOI:10.1021/jo00128a024

2.) Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration, Imao, Daisuke, Glasspoole, Ben W., Laberge, Veronique S., Crudden, Cathleen M., Journal of the American Chemical Society (2009), 131(14), 5024-5025. DOI:10.1021/ja8094075

3.) Palladium-Catalyzed Cross-Coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-Coupling Sequence, Takagi, Jun, Takahashi, Kou, Ishiyama, Tatsuo, Miyaura, Norio, Journal of the American Chemical Society (2002), 124(27), 8001-8006. DOI:10.1021/ja0202255

4.) Functionalized olefin cross-coupling to construct carbon-carbon bonds, Lo, Julian C., Gui, Jinghan, Yabe, Yuki, Pan, Chung-Mao, Baran, Phil S., Nature (London, United Kingdom) (2014), 516(7531), 343-348. DOI:10.1038/nature14006.

5.) The Synthesis of Highly Substituted Isoxazoles by Electrophilic Cyclization: An Efficient Synthesis of Valdecoxib, Waldo, Jesse P., Larock, Richard C., Journal of Organic Chemistry (2007), 72(25), 9643-9647. DOI:10.1021/jo701942e.

6.) Arenes to anilines and aryl ethers by sequential iridium-catalyzed borylation and copper-catalyzed coupling, Tzschucke, C. Christoph, Murphy, Jaclyn M., Hartwig, John F., Organic Letters (2007), 9(5), 761-764. DOI:10.1021/ol062902w

7.) A synthesis of allyboronates via the palladium(0)-catalyzed cross-coupling reaction of bis(pinacolato)diboron with allylic acetates, Ishiyama, Tatsuo, Ahiko, Taka-aki, Miyaura, Norio, Tetrahedron Letters (1996), 37(38), 6889-6892. DOI:10.1016/0040-4039(96)01505-5

8.) Rapid synthesis of 3-amino-imidazopyridines by a microwave-assisted four-component coupling in one pot, DiMauro, Erin F., Kennedy, Joseph M., Journal of Organic Chemistry (2007), 72(3), 1013-1016, DOI:10.1021/jo0622072

9.)  Iron-Catalyzed C(sp2)-H Bond Functionalization with Organoboron Compounds, Shang, Rui, Ilies, Laurean, Asako, Sobi, Nakamura, Eiichi, Journal of the American Chemical Society (2014), 136(41), 14349-14352. DOI:10.1021/ja5070763

10.) Copper-Promoted Coupling of Vinyl Boronates and Alcohols: A Mild Synthesis of Allyl Vinyl Ethers, Shade, Ryan E., Hyde, Alan M., Olsen, John-Carl, Merlic, Craig A., Journal of the American Chemical Society (2010), 132(4), 1202-1203. DOI:10.1021/ja907982w

Background: Facile addition of t-butyl synthons and substituents to halogenated scaffolds.

Molecular weight: 222.01 g/mol

Molecular Formula: C₉H₁₄BF₃O₂

CAS Number:  1011460-68-6

Storage: Store under dry conditions.

References: 

1.) Barnes-Seeman, David et al, Metabolically Stable tert-Butyl Replacement, ACS Medicinal Chemistry Letters, 4(6), 514-516; 2013.

2.)  Preparation of benzothiophene sulfonamides and related compounds that interact with glucokinase regulatory protein, Ashton, Kate et al, PCT Int. Appl., 2013173382, 21 Nov 2013.

3.)  Preparation of 4-pyridinylcyclohexene-1-carboxamides as TRPV1 antagonists, Gomtsyan, Arthur R. et al, PCT Int. Appl., 2009055629, 30 Apr 2009. 

4)  Preparation of carboxamide derivatives as antiviral compounds, Wang, Guangyi et al, PCT Int. Appl., 2015026792, 26 Feb 2015

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