Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 46, Pages 15227-15231Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809608
Keywords
amines; borylation; C-N activation; Lewis bases; radicals
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Funding
- 1000-Youth Talents Plan from the NSF of China [2167020084, 21673110]
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An efficient method for the metal-free deaminative borylation of alkylamines, using bis(catecholato) diboron as the boron source, to directly synthesize various alkyl potassium trifluoroborate salts is introduced. The key to this high reactivity is the utilization of pyridinium salt activated alkylamines, with a catalytic amount of a bipyridine-type Lewis base as a promoter. This transformation shows good functional-group compatibility (e.g., it is unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and can serve as a powerful synthetic tool for borylation of amine groups in complex compounds. Mechanistic experiments and computations suggest a mechanism in which the Lewis base activated B(2)cat(2) unit intercepts an alkyl radical generated by single-electron transfer (SET) from a boron-based reductant.
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