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Facile C−F Bond Activation Approach to FAMT‐Based Difluoromethyl‐BNCT Drug Candidates
Author(s) -
Yokawa Akitaka,
Hatanaka Miho,
Mikami Koichi
Publication year - 2021
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000211
Subject(s) - chemistry , boron , neutron capture , drug , lithium (medication) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , pharmacology , medicine , endocrinology
Lithium 1,3‐bis(2,6‐diisopropylphenyl)‐1,3,2‐diazaborolidinyl‐2‐uide activates the C−F linkage of fluoroform (CF 3 H) to provide air‐stable difluoromethylborane compounds. Computational analysis of S N 2‐type transition state for the C−F bond activation of fluoroform with boryllithium clarifies the mechanism involving the lithium dimeric species in the pre‐reaction complex. FAMT (=3‐fluoro‐ l ‐α‐methyl‐tyrosine)‐based difluoromethyl‐BNCT (boron neutron capture therapy) drug candidates is thus produced by the present C−F bond activation.