California Institute of Technology

University of California

Anton A Toutov

Robert H Grubbs

Kerry N Betz

Brian M Stoltz

Alexey Fedorov

Wenbo Liu

Andrew M Romine

Jennifer Marie Murphy

David P Schuman

Christopher Martin Waldmann

Nicholas A Swisher

Brian M Stolz

The present disclosure sets forth novel compounds and compositions including heteroaromatic silicon-fluoride-acceptors, which are useful for PET scanning. The present disclosure further includes novel methods ofF imaging for PET scanning, the methods comprising the preparation of conjugates and bioconjugates of biological ligands of interest with heteroaromatic silicon-fluoride-acceptors. In certain embodiments the invention is practiced in the form of a kit.

Heteroaromatic silicon-fluoride-acceptors useful forF labeling of molecules and biomolecules, and methods of preparing same

The present disclosure is directed to hydrosilyl amines and fluorosilyl amines and methods of making the same.

Hydrosilylamines and fluorosilylamines and methods of making the same

The present disclosure describes methods for silylating aromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.

Silylated derivatives of aromatic heterocycles

Heteroaromatic silicon-fluoride-acceptors useful for 18F labeling of molecules and biomolecules, and methods of preparing same

The present disclosure describes methods for silylating aromatic organic substrates, and associated chemical systems, said methods comprising or consisting essentially of contacting the aromatic organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate.

Silylations of aromatic substrates with base-activated organosilanes

The present disclosure is directed to methods for dehydrogenatively coupled hydrosilanes and alcohols, the methods comprising contacting an organic substrate having at least one organic alcohol moiety with a mixture of at least one hydrosilane and sodium and/or potassium hydroxide, the contacting resulting in the formation of a dehydrogenatively coupled silyl ether. The disclosure further described associated compositions and methods of using the formed products.

Hydroxide-catalyzed formation of silicon-oxygen bonds by dehydrogenative coupling of hydrosilanes and alcohols

The present invention is directed to compositions for silylating organic substrates containing C&#x2014;H or O&#x2014;H bonds, especially heteroaromatic substrates. The compositions are derived from the preconditioning of mixtures of hydrosilanes or organodisilanes with bases, including metal hydroxide and metal alkoxide bases. In some embodiments, the preconditioning results in the formation of reactive silicon hydride species.

Stable silylating reagents

The present disclosure is directed at methods of forming an N&#x2014;Si silyl bond, the method comprising contacting an organic substrate comprising an aromatic amine having at least one N&#x2014;H bond with a mixture comprising of (a) at least one hydrosilane and (b) at least one hydroxide or alkoxide, under conditions sufficient to form the N&#x2014;Si bond. The disclosure is further directed to the compositions involved in these methods and the products that result therefrom.

Preparation of aromatic-substituted silylamines by the dehydrogenative coupling of aromatic-substituted amine N&#x2014;H and Si&#x2014;H bonds

The present disclosure describes methods for silylating heteroaromatic derivatives, comprising the use of hydrosilanes and potassium hydroxide.

The present invention includes novel compounds and compositions including heteroaromatic Silicon-Fluoride-Acceptors, which are useful for PET scanning. The present invention further includes a novel method of 18F imaging for PET scanning, the method comprising the preparation of conjugates and bioconjugates of biological ligands of interest with heteroaromatic SiFAs. In one embodiment the invention is practiced in the form of a kit.

The present disclosure is directed at methods of forming an N&#x2014;Si silyl bond, the method comprising contacting an organic substrate comprising an aromatic amine having at least one N&#x2014;H bond with a mixture comprising of (a) at least one hydrosilane or hydrosiloxane and (b) at least one hydroxide or alkoxide, under conditions sufficient to form the N&#x2014;Si bond. The disclosure is further directed to the compositions involved in these methods and the products that result therefrom.

The present disclosure describes novel silylated heteroaromatic derivatives, including those prepared by methods comprising the use of hydrosilanes and at least one strong base, the definition of strong base now also including hydroxide, especially KOH.

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Pasadena, CA, United States of America

Anton A Toutov