A compound having a chemical formula according to Formula (I) is disclosed where one of Z.sub.1, Z.sub.2 and Z.sub.3 is and one of the Z.sub.1, Z.sub.2, and Z.sub.3 that is bonded to a carbon atom that is adjacent to the carbon atom bonded to is P(AR.sub.1)(AR.sub.2). Metal-based catalyst and pre-catalysts, such as nickel-based catalysts and precatalysts, where the metal is complexed to the compound are also disclosed. Methods of forming C(sp2)-N bonds are also disclosed.

A compound having a chemical formula according to Formula (I) is disclosed where one of Z.sub.1, Z.sub.2 and Z.sub.3 is and one of the Z.sub.1, Z.sub.2, and Z.sub.3 that is bonded to a carbon atom that is adjacent to the carbon atom bonded to is P(AR.sub.1)(AR.sub.2). Metal-based catalyst and pre-catalysts, such as nickel-based catalysts and precatalysts, where the metal is complexed to the compound are also disclosed. Methods of forming C(sp2)-N bonds are also disclosed.

Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.

Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound.

The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an amine; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound. The present disclosure further describes a one-pot method for coupling a first compound to a second compound.

A compound represented by the formula:

##STR00001## wherein R is selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; (ii) substituted or unsubstituted aryl; and (iii) substituted and unsubstituted alkylaryl; wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen and R.sup.2 and R.sup.3 may optionally be bridged by a polymethylene group; wherein when C=0 in R, the combined group R.sup.1 R.sup.2 is the same as the combined group R.sup.3 R.sup.4; and wherein when C=1 in R, each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen.

A compound represented by the formula:

##STR00001## wherein R is selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; (ii) substituted or unsubstituted aryl; and (iii) substituted and unsubstituted alkylaryl; wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen and R.sup.2 and R.sup.3 may optionally be bridged by a polymethylene group; wherein when C=0 in R, the combined group R.sup.1 R.sup.2 is the same as the combined group R.sup.3 R.sup.4; and wherein when C=1 in R, each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen.

The present invention provides a synthesis system that can synthesize aniline and/or styrene efficiently, a synthesis system that can synthesize butadiene (1,3-butadiene) efficiently, a rubber chemical for a tire which is synthesized from the aniline obtained by the synthesis system, a synthetic rubber for a tire which is synthesized from the styrene and/or butadiene obtained by the synthesis systems, and a pneumatic tire produced using the rubber chemical for a tire and/or the synthetic rubber for a tire. The present invention relates to a synthesis system for synthesizing aniline and/or styrene from an alcohol having two or more carbon atoms via an aromatic compound.