Selective C–F and C–H Activation of
Fluoroarenes by Fe(PMe3)4 and Catalytic Performance
of Iron Hydride in Hydrosilylation of Carbonyl Compounds
Version 2 2016-10-18, 16:14
Version 1 2016-09-30, 17:54
Posted on 2016-09-30 - 00:00
The reactions of
perfluorinated toluene (CF3C6F5),
pentafluoropyridine (C5NF5),
and hexafluorobenzene (C6F6) with the iron(0)
complex Fe(PMe3)4 were investigated. The Fe(I)
complexes (4-CF3C6F4)Fe(PMe3)4 (1), (4-C5NF4)Fe(PMe3)4 (2), and (C6F5)Fe(PMe3)4 (3) were obtained by
selective activation of the C–F bonds. However, under similar
reaction conditions, the reaction of Fe(PMe3)4 with perfluoronaphthalene (C10F8) afforded
a π-coordinated Fe(0) complex, (η4-1,2,3,4-C10F8)Fe(PMe3)3 (4), and the expected C–F bond activation reaction was not observed.
The expected iron hydride (C6F5)FeH(PMe3)4 (6) could be obtained in a yield
of 80% by the reaction of bromopentafluorobenzene with Fe(PMe3)4 and subsequent reduction with NaBH4. The molecular structures of complexes 2, 4, and 6 were determined by single-crystal X-ray diffraction.
Complexes 1–4 and 6 could
be used as catalysts for the hydrosilylation of carbonyl compounds.
Among them, complex 6 is the best catalyst. The selective
reduction of carbonyl groups of α,β-unsaturated aldehydes
and ketones was also realized with 6 as catalyst.
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Zheng, Tingting; Li, Junye; Zhang, Shumiao; Xue, Benjing; Sun, Hongjian; Li, Xiaoyan; et al. (2016). Selective C–F and C–H Activation of
Fluoroarenes by Fe(PMe3)4 and Catalytic Performance
of Iron Hydride in Hydrosilylation of Carbonyl Compounds. ACS Publications. Collection. https://doi.org/10.1021/acs.organomet.6b00546
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AUTHORS (8)
TZ
Tingting Zheng
JL
Junye Li
SZ
Shumiao Zhang
BX
Benjing Xue
HS
Hongjian Sun
XL
Xiaoyan Li
OF
Olaf Fuhr
DF
Dieter Fenske