Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 6, Pages 1965-1968Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409246
Keywords
boron; homogeneous catalysis; hydrogenation; Lewis acids; reduction
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Funding
- Cluster of Excellence Unifying Concepts in Catalysis of the Deutsche Forschungsgemeinschaft [EXC 314/2]
- Einstein Foundation (Berlin)
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The strong boron Lewis acid tris(pentafluorophenyl)borane, B(C6F5)(3), is shown to abstract a hydride from suitably donor-substituted cyclohexa-1,4-dienes, eventually releasing dihydrogen. This process is coupled with the FLP-type (FLP=frustrated Lewis pair) hydrogenation of imines and nitrogen-containing heteroarenes that are catalyzed by the same Lewis acid. The net reaction is a B(C6F5)(3)-catalyzed, i.e., transition-metal-free, transfer hydrogenation using easy-to-access cyclohexa-1,4-dienes as reducing agents. Competing reaction pathways with or without the involvement of free dihydrogen are discussed.
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