Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 9, Pages 2875-2878Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814081
Keywords
aldimines; aminoboranes; DFT Calculations; kinetics
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Funding
- U.S. Department of Energy, Office of Science, Basic Energy Sciences, Catalysis Science Program [DE-SC0009376]
- U.S. Department of Education
- National Science Foundation Graduate Research Fellowship Program [DGE-1650112]
- National Science Foundation [ACI-1548562]
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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.
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