Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water

The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite

Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water

The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reaction. We have demonstrated this methodology to work excellently in the modification of model tripeptides. Furthermore, through precursor directed biosynthesis, we have generated for the first time a new to nature brominated natural product bromo-cystargamide, and demonstrated the applicability of our reaction conditions to modify this novel metabolite

Chiral Co₃Y Propeller-Shaped Chemosensory Platforms Based on ¹⁹F-NMR

Two propeller-shaped chiral CoIII3YIII complexes built from fluorinated ligands are synthesized and characterized by single-crystal X-ray diffraction (SXRD), IR, UV–vis, circular dichroism (CD), elemental analysis, thermogravimetric analysis (TGA), electron spray ionization mass spectroscopy (ESI-MS), and NMR (1H, 13C, and 19F). This work explores the sensing and discrimination abilities of these complexes, thus providing an innovative sensing method using a 19F NMR chemosensory system and opening new directions in 3d/4f chemistry. Control experiments and theoretical studies shed light on the sensing mechanism, while the scope and limitations of this method are discussed and presented

Chiral Co3Y propeller-shaped chemosensory platforms based on 19F-NMR

Two propeller-shaped chiral CoIII3YIII complexes built from fluorinated ligands are synthesized and characterized by single-crystal X-Ray diffraction (SXRD), IR, UV-Vis, Circular Dichroism (CD), Elemental analysis, Thermogravimetric analysis (TGA), Electron Spray Ionization Mass Spectroscopy (ESI-MS) and NMR (1H, 13C and 19F). This work explores the sensing and discrimination abilities of these complexes, thus providing an innovative sensing method using a 19F NMR chemosensory system and opening new directions in 3d/4f chemistry. Control experiments and theoretical studies shed light on the sensing mechanism, while the scope and limitations of this method are discussed and presented

Chiral Co3Y propeller-shaped chemosensory platforms based on 19F-NMR

Two propeller-shaped chiral CoIII3YIII complexes built from fluorinated ligands are synthesized and characterized by single-crystal X-Ray diffraction (SXRD), IR, UV-Vis, Circular Dichroism (CD), Elemental analysis, Thermogravimetric analysis (TGA), Electron Spray Ionization Mass Spectroscopy (ESI-MS) and NMR (1H, 13C and 19F). This work explores the sensing and discrimination abilities of these complexes, thus providing an innovative sensing method using a 19F NMR chemosensory system and opening new directions in 3d/4f chemistry. Control experiments and theoretical studies shed light on the sensing mechanism, while the scope and limitations of this method are discussed and presented

Chiral Co₃Y Propeller-Shaped Chemosensory Platforms Based on ¹⁹F‑NMR

Two propeller-shaped chiral CoIII3YIII complexes built from fluorinated ligands are synthesized and characterized by single-crystal X-ray diffraction (SXRD), IR, UV–vis, circular dichroism (CD), elemental analysis, thermogravimetric analysis (TGA), electron spray ionization mass spectroscopy (ESI-MS), and NMR (1H, 13C, and 19F). This work explores the sensing and discrimination abilities of these complexes, thus providing an innovative sensing method using a 19F NMR chemosensory system and opening new directions in 3d/4f chemistry. Control experiments and theoretical studies shed light on the sensing mechanism, while the scope and limitations of this method are discussed and presented

Methods for the Direct Synthesis of Benzoxazoles from Halogenated Nitriles in Alcoholic Solvents.

Two complementary approaches for the direct synthesis of 2-dichloro- and 2-trichlorobenzoxazoles from 2-aminophenols and halogenated nitriles are reported. A green, noncatalyzed method was shown to proceed in an alc. solvent without the addn. of exogenous acid or base. This method provides a clean and robust synthesis of these important heterocycles, which contain a key functional group handle at the 2-position. A complementary platinum multifaceted catalysis approach was also developed in which the metal can catalyzes multiple mechanistically distinct processes. This method allows for an improved use of the metal catalyst vs stepwise protocols and provides increased flexibility in the choice of reaction conditions. [on SciFinder(R)