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Abstract: Primary aminoboranes (RNHBR2), which are readily available by spontaneous dehydrocoupling of amines and boranes cleanly react at room temperature with aldehydes to give aldimines. The overall transformation from amines to aldimines can be conveniently performed by a sequential one-pot reaction. This synthetic strategy is especially useful for electron poor and bulky amines which are reluctant to react with aldehydes under dehydration conditions. Using a Glorius robustness screen, we show that this methodology is chemoselective, and functional group tolerant. Computational and experimental data support the irreversible formation of the aldimine product in marked contrast with traditional methods. 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), which is supported by National Science Foundation grant number ACI-1548562 for provided computational resources. Research Data Curation Program, UC San Diego, La Jolla, 92093-0175 (https://lib.ucsd.edu/rdcp) Junor, Glen P.; Romero, Erik A.; Chen, Xi; Jazzar, Rodolphe; Bertrand, Guy (2019). Data From: Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis. UC San Diego Library Digital Collections. https://doi.org/10.6075/J00Z71HW Junor, Glen P.; Romero, Erik A.; Chen, Xi; Jazzar, Rodolphe; Bertrand, Guy (2019). Readily Available Primary Aminoboranes as Powerful Reagents for Aldimine Synthesis. Angew. Chem. Int. Ed. https://doi.org/10.1002/anie.201814081 Data pertaining to each computed pathway, for the reaction between aldehydes and aminoboranes, can be downloaded. Within each .zip file are a number of folders containing .log, .chk, and .fchk files for each species along the reaction coordinate. Some folders contain additional subfolders.
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Density functional calculations Kinetics Aminoboranes Aldimines