Neopentylboronic acid CAS: 701261-35-0 MDL: MFCD09750464
Molecular weight:Â 115.97 g/mol
Molecular Formula: C5H13BO2
CAS Number: 701261-35-0
Storage: Store at –20 °C, under dry conditions.
Synonyms: Â Â NA
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.