Exploration of mild copper-mediated coupling of organotrifluoroborates in the synthesis of thiirane-based inhibitors of matrix metalloproteinases |
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Authors: | Testero Sebastian A Bouley Renee Fisher Jed F Chang Mayland Mobashery Shahriar |
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Institution: | Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA |
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Abstract: | 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. |
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Keywords: | Thiirane Ullmann reaction Organotrifluoroborate salt Diaryl ether synthesis Cross-coupling |
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