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Beilstein J. Org. Chem. 2011, 7, 1379–1386, doi:10.3762/bjoc.7.162
Graphical Abstract
Scheme 1: Amino-hydroxyfluorination of alkynes reported by Nevado et al. [2].
Scheme 2: Proposed access to fluoromethylene pyrrolidines and piperidines.
Scheme 3: Cyclization of 1b under standard conditions.
Scheme 4: Proposed mechanism.
Scheme 5: Mechanistic probes.
Scheme 6: Cationic Au(I)-catalyzed reaction of 1a without Selectfluor.
Beilstein J. Org. Chem. 2010, 6, 709–712, doi:10.3762/bjoc.6.82
Figure 1: Representative complexes of N-heterocyclic carbenes and boranes (NHC–boranes).
Figure 2: Bertrand’s amino anthracenyl carbene trifluoroborane complex.
Scheme 1: Synthesis of stable CAAC–BF3 complexes 3a and 3b and in situ generation of CAAC–BH3 complex 4a.
Figure 3: X-Ray crystal structures of CAAC–BF3 complexes 3a (top) and 3b (bottom).