3-Acrylamidophenylboronic acid

Product Number: A10094; CAS Number: 99349-68-5

A10094 Technical Data Sheet 




3-Acrylamidophenylboronic acid CAS: 99349-68-5 MDL: MFCD09025755

Molecular weight: 115.97 g/mol

 Molecular Formula: C9H10BNO3

CAS Number:  99349-68-5

Storage: Store at –20 °C , under  dry conditions.

Synonyms:   99349-68-5, 3-Acrylamidophenylboronic acid, (3-Acrylamidophenyl)boronic acid, (M-Acrylamidophenyl)boronic acid, [3-(prop-2-enoylamino)phenyl]boronic acid

[3-(prop-2-enamido)phenyl]boronic acid, 3-(Acrylamido)phenylboronic acid

ACMC-209scf, SCHEMBL235432

Uses: Transition Metal Coupling Reactions

Selected References

Boronic Acid Derivative Coupling Reactions

1.) Altenhoff, Gereon, Richard Goddard, Christian W. Lehmann, and Frank. Glorius.   Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands with Restricted Flexibility for Catalysis.   Journal of the American Chemical Society 126, no.   (2004): 15195–201. https://doi.org/10.1021/ja045349r.

2.) Arvela, Riina K., Nicholas E. Leadbeater, Michael S. Sangi, Victoria A. Williams, Patricia Granados, and Robert D. Singer.   A Reassessment of the Transition-Metal Free Suzuki-Type Coupling Methodology.   Journal of Organic Chemistry 70, no.   (2005): 161–68. https://doi.org/10.1021/jo048531j.

3.) Billingsley, Kelvin, and Stephen L. Buchwald.   Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters.   Journal of the American Chemical Society 129, no.   (2007): 3358–66. https://doi.org/10.1021/ja068577p.

4.) Billingsley, Kelvin L., Kevin W. Anderson, and Stephen L. Buchwald.   A Highly Active Catalyst for Suzuki-Miyaura Cross-Coupling Reactions of Heteroaryl Compounds.   Angewandte Chemie, International Edition 45, no.   (2006): 3484–88. https://doi.org/10.1002/anie.200600493.

5.) Gillis, Eric P., and Martin D. Burke.   A Simple and Modular Strategy for Small Molecule Synthesis: Iterative Suzuki-Miyaura Coupling of B-Protected Haloboronic Acid Building Blocks.   Journal of the American Chemical Society 129, no.   (2007): 6716–17. https://doi.org/10.1021/ja0716204.

6.) Herradura, Prudencio S., Kathleen A. Pendola, and R. Kiplin. Guy.   Copper-Mediated Cross-Coupling of Aryl Boronic Acids and Alkyl Thiols.   Organic Letters 2, no.   (2000): 2019–22. https://doi.org/10.1021/ol005832g.

7.) Kataoka, Noriyasu, Quinetta Shelby, James P. Stambuli, and John F. Hartwig.   Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C-C, C-N, and C-O Bond-Forming Cross-Couplings.   Journal of Organic Chemistry 67, no.   (2002): 5553–66. https://doi.org/10.1021/jo025732j.

8.) Kinzel, Tom, Yong Zhang, and Stephen L. Buchwald.   A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids.   Journal of the American Chemical Society 132, no.   (2010): 14073–75. https://doi.org/10.1021/ja1073799.

9.) Knapp, David M., Eric P. Gillis, and Martin D. Burke.   A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates.   Journal of the American Chemical Society 131, no.   (2009): 6961–63. https://doi.org/10.1021/ja901416p.

10.) Liebeskind, Lanny S., and Jiri. Srogl.   Thiol Ester-Boronic Acid Coupling. A Mechanistically Unprecedented and General Ketone Synthesis.   Journal of the American Chemical Society 122, no.   (2000): 11260–61. https://doi.org/10.1021/ja005613q.

11.) McGuinness, David S., and Kingsley J. Cavell.   Donor-Functionalized Heterocyclic Carbene Complexes of Palladium(II): Efficient Catalysts for C-C Coupling Reactions.   Organometallics 19, no.   (2000): 741–48. https://doi.org/10.1021/om990776c.

12.) Miyaura, N., T. Yanagi, and A. Suzuki.   The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases.   Synthetic Communications 11, no.   (1981): 513–19. https://doi.org/10.1080/00397918108063618.

13.) Miyaura, Norio.   Organoboron Compounds.   Topics in Current Chemistry 219, no.   (2002): 11–59.

14.) Nguyen, Hanh Nho, Xiaohua Huang, and Stephen L. Buchwald.   The First General Palladium Catalyst for the Suzuki-Miyaura and Carbonyl Enolate Coupling of Aryl Arenesulfonates.   Journal of the American Chemical Society 125, no.   (2003): 11818–19. https://doi.org/10.1021/ja036947t.

15.) Qiao, Jennifer X., and Patrick Y. S. Lam.   Copper-Promoted Carbon-Heteroatom Bond Cross-Coupling with Boronic Acids and Derivatives.   Synthesis, no.   (2011): 829–56. https://doi.org/10.1055/s-0030-1258379.

16.) Seiple, Ian B., Shun Su, Rodrigo A. Rodriguez, Ryan Gianatassio, Yuta Fujiwara, Adam L. Sobel, and Phil S. Baran.   Direct C-H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids.   Journal of the American Chemical Society 132, no.   (2010): 13194–96. https://doi.org/10.1021/ja1066459.

17.) Shirota, Yasuhiko, Motoi Kinoshita, Tetsuya Noda, Kenji Okumoto, and Takahiro. Ohara.   A Novel Class of Emitting Amorphous Molecular Materials as Bipolar Radical Formants: 2-{4-[Bis(4-Methylphenyl)Amino]Phenyl}-5-(Dimesitylboryl)Thiophene and 2-{4-[Bis(9,9-Dimethylfluorenyl)Amino]Phenyl}-5-(Dimesitylboryl)Thiophene.   Journal of the American Chemical Society 122, no.   (2000): 11021–22. https://doi.org/10.1021/ja0023332.

18.) Stambuli, James P., Ryoichi Kuwano, and John F. Hartwig.   Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room Temperature.   Angewandte Chemie, International Edition 41, no.   (2002): 4746–48. https://doi.org/10.1002/anie.200290036.

19.) Tsuboyama, Akira, Hironobu Iwawaki, Manabu Furugori, Taihei Mukaide, Jun Kamatani, Satoshi Igawa, Takashi Moriyama, et al.   Homoleptic Cyclometalated Iridium Complexes with Highly Efficient Red Phosphorescence and Application to Organic Light-Emitting Diode.   Journal of the American Chemical Society 125, no.   (2003): 12971–79. https://doi.org/10.1021/ja034732d.

20.) Wang, Dong-Hui, Masayuki Wasa, Ramesh Giri, and Jin-Quan. Yu.   Pd(II)-Catalyzed Cross-Coupling of Sp3 C-H Bonds with Sp2 and Sp3 Boronic Acids Using Air as the Oxidant.   Journal of the American Chemical Society 130, no.   (2008): 7190–91. https://doi.org/10.1021/ja801355s.

21.) Wright, Stephen W., David L. Hageman, and Lester D. McClure.   Fluoride-Mediated Boronic Acid Coupling Reactions.   Journal of Organic Chemistry 59, no.   (1994): 6095–97. https://doi.org/10.1021/jo00099a049.



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