Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases.
The copper-mediated and non-basic oxidative cross-coupling of organotrifluoroborates with phenols was applied to elaboration of the structures of thiirane-based inhibitors of matrix metalloproteinases. By revision of the synthetic sequence to allow this cross-coupling as the final step, and taking advantage of the neutral nature of organotrifluoroborate cross-coupling, a focussed series of inhibitors showing aryloxy and alkenyloxy replacement of the phenoxy substituent was prepared. This reaction shows exceptional promise as an alternative to the classic copper-mediated but strongly basic Ullmann reaction, for the diversification of ether segments within base-labile lead structures.
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Sebastian A
SA
Testero
Renee
R
Bouley
Jed F
JF
Fisher
Mayland
M
Chang
Shahriar
S
Mobashery
D001881:Borates / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D061965:Matrix Metalloproteinase Inhibitors; D015394:Molecular Structure; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry
D001881:Borates; D004791:Enzyme Inhibitors; D006845:Hydrocarbons, Fluorinated; D061965:Matrix Metalloproteinase Inhibitors; D013440:Sulfides; D003300:Copper; C013523:ethylene sulfide
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