Provided are methods of forming a carbon-carbon bond between a first compound and a second compound through a hydroarylation chemical reaction. The methods include contacting the first compound and the second compound in the presence of an acid catalyst. The methods include forming a carbon-carbon bond wherein the first compound includes a first aryl group that is electron-deficient. Provided is a method of generating a quaternary carbon through a hydroarylation chemical reaction.

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I). ##STR00001##

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

A compound of formula (I) wherein M is Pd(II) or Ni(II); X is a halide; R.sub.1 and R.sub.2 are independently organic groups having 1-20 carbon atoms, or R.sub.1 and R.sub.2 are linked to form a ring structure with the phosphorus atom; R.sub.3 is an organic group having 1-20 carbon atoms; provided that R.sub.1, R.sub.2, R.sub.3 are not each phenyl.

##STR00001##

Provided herein, in part, is a new class of sterically bulky, easily prepared N-heterocyclic carbene (NHC) ligands of Formula I, or a salt, solvate, geometric isomer, or stereoisomer thereof. The ligands are readily synthetically accessible exploiting the cost-effective, modular alkylation of anilines. The NHC ligands of the present disclosure can be used to prepare effective catalysts with transition metals, including the compound of Formula II, or a salt, solvate, geometric isomer, or stereoisomer thereof. In certain embodiments, the transition metal is Pd.

The invention discloses a mixed Ni(II) complex containing bisoxazoline-derived nitrogen heterocyclic carbene ligand and phosphite ligand and application thereof; the chemical formula of the mixed Ni(II) complex is Ni(NHC)[P(OR).sub.3]X.sub.2, wherein R is ethyl or isopropyl, X is bromine or chlorine, and NHC is a bisoxazoline-derived nitrogen heterocyclic carbene ligand. In the presence of magnesium shavings, the mixed Ni(II) complex containing bisoxazoline-derived nitrogen heterocyclic carbene ligand and phosphite ligand of the present invention can catalyze low-activity chlorinated aromatic hydrocarbons and fluorinated aromatic hydrocarbons with chlorinated benzyl compounds, respectively, reductive cross-coupling reaction at a single temperature, generating a diarylmethane compound in one step, providing a new method for the synthesis of diarylmethane compounds.

The present disclosure relates to an ionic liquid composition and a process for its preparation. The process of the present disclosure is simple, single pot and efficient process for preparing the ionic liquid composition which is effective in a Friedel Craft reaction like, alkylation reaction, trans-alkylation, and acylation. The present disclosure envisages an ionic liquid composition comprising at least one metal hydroxide; at least one metal halide; and at least one solvent. Also envisaged is a process for preparing an ionic liquid composition. The process comprises mixing in a reaction vessel, at least one metal hydroxide and at least one metal halide in the presence of at least one solvent under a nitrogen atmosphere and continuous stirring followed by cooling under continuous stirring to obtain the ionic liquid composition.

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

##STR00001##

A method includes: providing a mixture including at least one alkyl tosylate and a Grignard reagent; and reacting the at least one alkyl tosylate with the Grignard reagent in a C—C coupling reaction mechanism to form a branched aliphatic alcohol.