Document Detail

Taking the F out of FLP. Simple Lewis acid-base pairs for mild reductions with neutral boranes via borenium ion catalysis.
MedLine Citation:
PMID:  23030065     Owner:  NLM     Status:  Publisher    
Discrete 3-coordinate borenium salts 1c and 1d are accessed by cooperative Lewis acid/base pair-mediated heterolytic splitting of the B-H bond in pinacolborane by B(C6F5)3•DABCO or Ph3C+/DABCO, respectively. The resulting salts are competent catalysts in the reduction of a broad range of imines and can be generated in-situ. Moreover, a mechanistic framework for borenium-catalysis is proposed based on experimental evidence. This suggests the reaction proceeds by borenium-activation of the imine substrate followed by counterintuitive hydride delivery from HBPin (with the assistance of DABCO) rather than from the HB(C6F5)3- anion, contrary to typical mechanisms of reduction in FLP systems.
Patrick Eisenberger; Adrian M Bailey; Cathleen Marie Crudden
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-2
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-3     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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