Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 37, Pages 13032-13036Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603328
Keywords
B-H bond activation; catecholborane; C-N bond cleavage; N-heterocyclic carbene; ring expansion reaction
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Funding
- DFG
- Universitat Wurzburg
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We report the reactions of catecholborane (HBcat; 1) with unsaturated and saturated NHCs as well as CAAC(Me). Mono-NHC adducts of the type HBcat center dot NHC (NHC=nPr(2)Im, iPr(2)Im, iPr(2)ImMe, and Dipp(2)Im) were obtained by stoichiometric reactions of HBcat with the unsaturated NHCs. The reaction of CAAC(Me) with HBcat yielded the B-H activated product CAAC(Me)(H) Bcat via insertion of the carbine-carbon atom into the B-H bond. The saturated NHC Dipp(2)SIm reacted in a 2: 2 ratio yielding an NHC ring-expanded product at room temperature forming a six-membered -B-C=N-C=C-N- ring via C-N bond cleavage and further migration of the hydrides from two HBcat molecules to the former carbene-carbon atom.
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