Facile Synthesis of α‑N-Heterocyclic Carbene-Boryl Ketones from N‑Heterocyclic Carbene-Boranes and Alkenyl Triflates
Posted on 2019-07-23 - 02:13
Reactions
of readily available alkenyl triflates with N-heterocyclic
carbene (NHC)-boranes in the presence of diisopropyl ethyl amine provided
about three dozen stable α-NHC-boryl ketones. Isolated yields
were typically 40–56% for B-unsubstituted NHC-boranes (NHC-BH3), and somewhat lower for NHC-boranes with B-substituents
(NHC-BH2R). The requisite alkenyl triflates can be made
separately or prepared in situ from either ketones or alkynes. The
experimental evidence supports a radical chain mechanism that involves
the following: (1) addition of an NHC-boryl radical to the alkenyl
triflate, (2) fragmentation to give the α-NHC-boryl ketone,
SO2, and trifluoromethyl radical, and (3) hydrogen abstraction
by trifluoromethyl radical from the starting NHC-borane to return
the NHC-boryl radical along with trifluoromethane. Reactions 1 and
3 are both new and evidently rather fast.
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Dai, Wen; Geib, Steven J.; Curran, Dennis P. (2019). Facile Synthesis of α‑N-Heterocyclic Carbene-Boryl Ketones from N‑Heterocyclic Carbene-Boranes and Alkenyl Triflates. ACS Publications. Collection. https://doi.org/10.1021/jacs.9b05547
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AUTHORS (3)
WD
Wen Dai
SG
Steven J. Geib
DC
Dennis P. Curran