University of California

Bp Corporation North America Inc.

California Institute of Technology

F Dean Toste

Sanil Sreekumar

Amit A Gokhale

Alexis T Bell

Gorkem Gunbas

Eric R Sacia

Balakrishnan Madhesan

George E Arab

Robert H Grubbs

Christopher J Chang

Douglas S Clark

Harvey W Blanch

Joseph B Binder

Adam Grippo

Shylesh Sankaranarayanapillai

Arnab Kumar Chatterjee

Gregory Hamilton

Jeffrey Yung Wu

John P Morgan

Martin E Carrera

Tina M Trnka

Tae-Lim Choi

Daniel P Sanders

Matthias Scholl

Jennifer A Love

James Patrick O'Neil

Steven D Goldberg

Anbarasan Pazhamalai

Konstantinos A Goulas

Zachary C Baer

Zach Baer

ShiXian Lin

Pazhamalai Anbarasan

XiaoYu Yang

Mark Daniel Levin

Alec H Christian

Patti Zhang

Vivek Rauniyar

Aaron D Lackner

Robert J Phipps

Hunter Shunatona

Natalja Frueh

Yiming Wang

Jigar Patel

Takashi Honjo

Paul A Willems

Chemoselective conjugation is achieved through redox reactivity by reacting an N-transfer oxidant with a thioether substrate in a redox reaction in an aqueous environment to form a conjugation product. In embodiments, Redox-Activated Chemical Tagging (ReACT) strategies for methionine-based protein functionalization. Oxaziridine (Ox) compounds serve as oxidant-mediated reagents for direct functionalization by converting methionine to the corresponding sulfimide conjugation product.

Redox-based reagents for methionine bioconjugation

Au(III) complexes for [F] trifluoromethylation and methods for producing the same are disclosed. A gold complex comprises Au(CF)LR, wherein L comprises a solubility supporting ligand and R comprises an organic substituent. The Au(III) complex can be used to prepare a positron emitting isotope that can be used as tracers for positron emitting tomography (PET) scans.

Au(III) complexes for [18F] Trifluoromethylation and methods for producing the same

Urea-oxaziridines

Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.

Methods for producing cyclic and acyclic ketones

Provided herein are methods for producing &#x3b1;,&#x3b2;-unsaturated ketones from the condensation of methyl ketones in the presence of an amine catalyst. Such amine catalysts may be supported, for example, on a silica-alumina support. Such amine catalysts may be used in the presence of an additional acid. The &#x3b1;,&#x3b2;-unsaturated ketones may be produced by dimerization and/or timerization of the methyl ketones. Such &#x3b1;,&#x3b2;-unsaturated ketones may be suitable for use in producing fuels, gasoline additives, and/or lubricants, or precursors thereof. The methyl ketones may be obtained from renewable sources, such as by the fermentation of biomass.

Methods for producing fuels, gasoline additives, and lubricants using amine catalysts

Provided herein are methods for producing ketone(s) from the condensation of methyl ketone(s) and alcohol(s) in the presence of an amine catalyst and a metal catalyst. Such amine catalysts may be supported, for example, on a silica-alumina support. Such ketones may be suitable for use in producing fuels, gasoline additives, and/or lubricants, or precursors thereof. The methyl ketone(s) and/or alcohol(s) may be obtained from renewable sources, such as by fermentation of biomass.

The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. A largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is broadly applicable to a number of different reaction pathways, including to the enantioselective fluorocyclization of olefins, and dearomatization of aromatic systems with a cationic electrophile-transferring (e.g., fluorinating) agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity. The compounds and methods of the invention are of particular value, especially considering the scarcity of alternative approaches.

Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst

The present disclosure provides methods to produce ketones suitable for use as fuels and lubricants by catalytic conversion of an acetone-butanol-ethanol (ABE) fermentation product mixture that can be derived from biomass.

Method to convert fermentation mixture into fuels

The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.

Methods to produce fuels

The present disclosure generally relates to the production of fuels, gasoline additives, and/or lubricants, and precursors thereof. The compounds used to produce the fuels, gasoline additives, and/or lubricants, and precursors thereof may be derived from biomass. The fuels, gasoline additives, and/or lubricants, and precursors thereof may be produced by a combination of intermolecular and/or intramolecular aldol condensation reactions, Guerbet reactions, hydrogenation reactions, and/or oligomerization reactions.

Methods for producing fuels, gasoline additives, and lubricants

The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.

Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts

Methods are provided for carrying out nucleophilic addition reactions using oxo, sulfido or amido complexes of transition metals as reaction catalysts. Exemplary catalysts are oxo complexes of Group 7 transition metals, with rhenium (V) oxo complexes, including dioxo complexes, preferred. Nucleophilic addition reactions that can be catalyzed using the present methods include silylation, hydrosilylation, hydroamination, silylmetalation, carbometalation, aldol reactions, hydro- and carbometalation initiated cyclization/polymerization, and epoxide/aziridine opening. The invention also pertains to novel transition metal complexes that have utility in catalyzing such reactions.

Transition metal oxo, sulfido and amido complexes as catalysts of nucleophilic addition reactions

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Piedmont, CA, United States of America

F Dean Toste