10.1002/anie.201814081
Angewandte Chemie International Edition
COMMUNICATION
Synth. Catal. 2017, 359, 2375; i) S. Wubbolt, M. S. Maji, E. Irran, M.
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In summary, we have shown that primary aminoboranes, which
are readily available by spontaneous dehydrocoupling of amines
and boranes,[1] are powerful tools for the preparation of
aldimines. The overall transformation from amines to aldimines
can be conveniently performed by a sequential one-pot reaction.
The method is shown to be chemoselective, functional group
tolerant, and widely applicable to various amines, aldehydes and
boranes. Computational and experimental data support the
irreversible formation of the aldimine, which is mechanistically
orthogonal to traditional methods. We are currently investigating
other potential applications for this class of ambiphilic primary
aminoborane reagents.
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Acknowledgements
[13] Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215.
[14] G. A. Petersson, M. A. Al-Laham, J. Chem. Phys. 1991, 94, 6081.
[15] Relevant considerations for computational methods: H. Ryu, J. Park, H. K.
Kim, J. Y. Park, S.-T. Kim, M.-H. Baik, Organometallics 2018, 37, 3228.
[16] Output files from DFT calculations can be viewed and downloaded from
This work was supported by the U.S. Department of Energy,
Office of Science, Basic Energy Sciences, Catalysis Science
Program, under Award No. DE-SC0009376. Thanks are due to
the U.S. Department of Education for a GAANN fellowship
(E.A.R.), and to the Alfred P. Sloan Foundation’s University
Centre for Exemplary Mentoring (G.P.J.). This material is based
upon work supported by the National Science Foundation
Graduate Research Fellowship Program under Grant No. (DGE-
1650112; G.P.J.). Any opinions, findings, and conclusions or
recommendations expressed in this material are those of the
author(s) and do not necessarily reflect the views of the National
Science Foundation. We also acknowledge the Keck Foundation
as well as the Extreme Science and Engineering Discovery
Environment (XSEDE),[19] which is supported by National
Science Foundation grant number ACI-1548562 for provided
computational resources.
the
[17] Additional calculations with range of amines and aldehydes are
available in the supporting information section.
[18] CCDC 1883939 (14), 1883941
Py) and 1883940 (19) contain the
UC
San
Diego
Library
Digital
Collections
at:
a
(I
supplementary crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge Crystallographic Data Centre.
[19] J. Towns, T. Cockerill, M.l Dahan, I. Foster, K. Gaither, A. Grimshaw,
V.Hazlewood, S. Lathrop, D. Lifka, G. D. Peterson, R. Roskies, J. R. Scott,
N. Wilkins-Diehr, Comput. Sci. Eng. 2014, 16, 62.
Keywords: Aminoboranes • Aldimines • Density Functional
Calculations • Kinetics
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