Direct Synthetic Route to Functionalized 1,2-Azaborinines†

作者: Holger Braunschweig , K. Geetharani , J. Oscar C. Jimenez-Halla , Marius Schäfer

DOI: 10.1002/ANIE.201309707

关键词:

摘要: A new catalytic synthetic route to functionalized 1,2-azaborinines has been developed by the [2+2]/[2+4] cycloaddition reactions of di-tert-butyliminoboranes and alkynes in presence a rhodium catalyst. The first examples ferrocene-functionalized azaborinines have synthesized using this strategy. Moreover, regioselectivity reaction can be controlled formation an intermediate 1,2-azaborete complex, which results isolation azaborinine boronic ester. NH-containing BN isostere elimination isobutene from N(tBu) group under thermolytic conditions also achieved. Theoretical studies give further insight into group.

参考文章(75)
S. Aldridge, C. Bresner, I. A. Fallis, S. J. Coles, M. B. Hursthouse, Multidentate Lewis acids: synthesis, structure and mode of action of a redox-based fluoride ion sensor Chemical Communications. pp. 740- 741 ,(2002) , 10.1039/B200828A
Michael J.D Bosdet, Warren E Piers, B-N as a C-C substitute in aromatic systems Canadian Journal of Chemistry. ,vol. 87, pp. 8- 29 ,(2009) , 10.1139/V08-110
Masaaki Sugie, Harutoshi Takeo, Chi Matsumura, Microwave spectrum of aminoborane, BH2NH2 Chemical Physics Letters. ,vol. 64, pp. 573- 575 ,(1979) , 10.1016/0009-2614(79)80247-X
Jean-Hugues Fournier, Thierry Maris, James D. Wuest, Wenzhuo Guo, Elena Galoppini, Molecular Tectonics. Use of the Hydrogen Bonding of Boronic Acids To Direct Supramolecular Construction Journal of the American Chemical Society. ,vol. 125, pp. 1002- 1006 ,(2003) , 10.1021/JA0276772
Julia B. Heilmann, Yang Qin, Frieder Jäkle, Hans-Wolfram Lerner, Matthias Wagner, Boron-bridged poly(ferrocenylene)s as promising materials for nanoscale molecular wires Inorganica Chimica Acta. ,vol. 359, pp. 4802- 4806 ,(2006) , 10.1016/J.ICA.2006.05.009
Holger Braunschweig, Regina Dirk, Matthias Müller, Paul Nguyen, Rui Resendes, Derek P. Gates, Ian Manners, Einbau eines Elements der ersten Achterperiode in die Brücke eines gespannten Metallocenophans: Synthese eines borverbrückten [1]Ferrocenophans Angewandte Chemie. ,vol. 109, pp. 2433- 2435 ,(1997) , 10.1002/ANGE.19971092114
Michael J. D. Bosdet, Cory A. Jaska, Warren E. Piers, Ted S. Sorensen, Masood Parvez, Blue fluorescent 4a-Aza-4b-boraphenanthrenes. Organic Letters. ,vol. 9, pp. 1395- 1398 ,(2007) , 10.1021/OL070328Y
Zachary M. Hudson, Suning Wang, Impact of donor-acceptor geometry and metal chelation on photophysical properties and applications of triarylboranes. Accounts of Chemical Research. ,vol. 42, pp. 1584- 1596 ,(2009) , 10.1021/AR900072U
V. Lefèvre, J. L. Ripoll, Y. Dat, S. Joantéguy, V. Métail, A. Chrostowska-Senio, G. Pfister-Guillouzo, Flash Vacuum Thermolysis: First Gas-Phase Generation of Unhindered Silylidenephosphanes and Characterization by Photoelectron Spectroscopy Organometallics. ,vol. 16, pp. 1635- 1640 ,(1997) , 10.1021/OM960914N