Organic Letters
Letter
(14) For an authoritative overview, see: Ni, C.; Hu, J. Chem. Soc. Rev.
2016, 45, 5441−5454.
and N. Gajic are kindly acknowledged for X-ray analysis. We
are grateful to D. Dobusch for HRMS measurements.
(15) (a) Zhang, W.; Zhu, L.; Hu, J. Tetrahedron 2007, 63, 10569−
10575. See also: (b) Wang, L.; Wei, J.; Wu, R.; Cheng, G.; Li, X.; Hu,
J.; Hu, Y.; Sheng, R. Org. Chem. Front. 2017, 4, 214−223.
(16) (a) Monticelli, S.; Pace, V. Aust. J. Chem. 2018, 71, 473−475.
Scattered applications of labeled [18F]-FIM in heteroatom derivatiza-
tion for preparing radioligands can be found. See for example:
(b) Zhang, M.-R.; Maeda, J.; Ogawa, M.; Noguchi, J.; Ito, T.; Yoshida,
Y.; Okauchi, T.; Obayashi, S.; Suhara, T.; Suzuki, K. J. Med. Chem.
2004, 47, 2228−2235. Notably, previously reported uses of labeled
FIM were found of limited reproducibility, presumably as a
consequence of the instability of the products. See: (c) Zhang, M.-
R.; Ogawa, M.; Furutsuka, K.; Yoshida, Y.; Suzuki, K. J. Fluorine Chem.
2004, 125, 1879−1886. While this manuscript was under review, a
paper on the fluoromethomethylation of nitrogen heterocyclic
compounds with FIM has been published, see: (d) Wang, R.; Ding,
(17) (a) Parisi, G.; Colella, M.; Monticelli, S.; Romanazzi, G.;
Holzer, W.; Langer, T.; Degennaro, L.; Pace, V.; Luisi, R. J. Am. Chem.
Soc. 2017, 139, 13648−13651. (b) Castoldi, L.; Monticelli, S.;
Senatore, R.; Ielo, L.; Pace, V. Chem. Commun. 2018, 54, 6692−6704.
Recently, our group applied CHF2-type carbanions in difluoromethy-
lative homologations, see: (c) Miele, M.; D’Orsi, R.; Sridharan, V.;
Holzer, W.; Pace, V. Chem. Commun. 2019, 55, 12960−12963.
(d) Miele, M.; Citarella, A.; Micale, N.; Holzer, W.; Pace, V. Org. Lett.
2019, 21, 8261−8265.
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