The invention generally relates to methods of making substituted arenes via direct C—H, C—O, C—S, or C—N bond conversion and methods of synthesizing isotopically-labeled substituted arenes via direct carbon-halogen bond conversion. The invention also relates to anaerobic catalyst systems comprising an acridinium photocatalyst and a nucleophile selected from a halide, a cyanide, and an isotopically-labeled amine. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

The invention generally relates to methods of making substituted arenes via direct C—H, C—O, C—S, or C—N bond conversion and methods of synthesizing isotopically-labeled substituted arenes via direct carbon-halogen bond conversion. The invention also relates to anaerobic catalyst systems comprising an acridinium photocatalyst and a nucleophile selected from a halide, a cyanide, and an isotopically-labeled amine. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

A novel method of producing 1-chloro-3-(4-chlorophenoxy)benzene can include performing hydrogenation reduction of 1-bromo-2-chloro-4-(4-chlorophenoxy)benzene or 1-bromo-4-chloro-2-(4-chlorophenoxy)benzene.

A novel method of producing 1-chloro-3-(4-chlorophenoxy)benzene can include performing hydrogenation reduction of 1-bromo-2-chloro-4-(4-chlorophenoxy)benzene or 1-bromo-4-chloro-2-(4-chlorophenoxy)benzene.

Provided are 9-dechlorochrysophaentin analog compounds and the synthesis process thereof. The disclosed compound have remarkable antimicrobial activities that are comparable to, or even more potent than, the natural product chrysophaentin A. Also provided are method of inhibiting bacterial growth or treating bacterial infection by administering an effective amount of the disclosed compounds.

The invention is directed to ruthenium-based metathesis catalysts of the Grubbs-Hoveyda type. The new 2-aryloxy-substituted ruthenium catalysts described herein reveal rapid initiation behavior. Further, the corresponding styrene-based precursor compounds are disclosed. The catalysts are prepared in a cross-metathesis reaction starting from styrene-based precursors which can be prepared in a cost-effective manner.

The new Grubbs-Hoveyda type catalysts are suitable to catalyze ring-closing metathesis (RCM), cross metathesis (CM) and ring-opening metathesis polymerization (ROMP). Low catalyst loadings are necessary to convert a wide range of substrates including more complex and critical substrates via metathesis reactions at low to moderate temperatures in high yields within short reaction times.

The invention is directed to ruthenium-based metathesis catalysts of the Grubbs-Hoveyda type. The new 2-aryloxy-substituted ruthenium catalysts described herein reveal rapid initiation behavior. Further, the corresponding styrene-based precursor compounds are disclosed. The catalysts are prepared in a cross-metathesis reaction starting from styrene-based precursors which can be prepared in a cost-effective manner.

The new Grubbs-Hoveyda type catalysts are suitable to catalyze ring-closing metathesis (RCM), cross metathesis (CM) and ring-opening metathesis polymerization (ROMP). Low catalyst loadings are necessary to convert a wide range of substrates including more complex and critical substrates via metathesis reactions at low to moderate temperatures in high yields within short reaction times.

A crosslinking agent includes a compound represented by a formula (1), ##STR00001##
wherein R.sup.1, R.sup.2, and R.sup.3 are independently a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, or a substituted or unsubstituted aryl group, a plurality of R.sup.1 are identical to or different from each other, a plurality of R.sup.2 are identical to or different from each other, and a plurality of R.sup.3 are identical to or different from each other, provided that at least one of R.sup.1, R.sup.2, and R.sup.3 is a hydrogen atom, and at least one of R.sup.1, R.sup.2, and R.sup.3 is a fluorine atom or a fluorine atom-containing group; m is an integer from 2 to 6; l is an integer from 0 to 2; and each hydrogen on the benzene ring(s) may be substituted.

A crosslinking agent includes a compound represented by a formula (1), ##STR00001##
wherein R.sup.1, R.sup.2, and R.sup.3 are independently a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, or a substituted or unsubstituted aryl group, a plurality of R.sup.1 are identical to or different from each other, a plurality of R.sup.2 are identical to or different from each other, and a plurality of R.sup.3 are identical to or different from each other, provided that at least one of R.sup.1, R.sup.2, and R.sup.3 is a hydrogen atom, and at least one of R.sup.1, R.sup.2, and R.sup.3 is a fluorine atom or a fluorine atom-containing group; m is an integer from 2 to 6; l is an integer from 0 to 2; and each hydrogen on the benzene ring(s) may be substituted.

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO.sub.2F.sub.2 to a reaction mixture; reacting the SO.sub.2F.sub.2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO.sub.2F.sub.2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO.sub.2F.sub.2, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.