The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

A production method by which a biarylphosphine useful as a Buchwald phosphine ligand can be obtained in high purity is provided through an industrially advantageous process. The production method of a biarylphosphine comprises a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative with a benzene derivative to obtain a biphenyl derivative, and a step B of the reacting the biphenyl derivative with a halogenated phosphine. In the step A, the charge molar ratio of the halogenated benzene derivative to the benzene derivative is preferably 1.0 to 5.0.

The invention relates to lithium alkyl aluminates according to the general formula Li[AlR.sub.4] and to a method for preparing same, starting from LiAlH.sub.4 and RLi in an aprotic solvent. The invention also relates to compounds according to the general formula Li[AlR.sub.4] which can be obtained using the claimed method, and to the use thereof. The invention also relates to the use of a lithium alkyl aluminate Li[AlR.sub.4] as a transfer reagent for transferring at least one radical R to an element halide or metal halide and to a method for transferring at least one radical R to a compound E(X).sub.q for preparing a compound according to the general formula E(X).sub.q-pR.sub.p, where E=aluminium, gallium, indium, thallium, germanium, tin, lead, antimony, bismuth, zinc, cadmium, mercury, or phosphorus, X=halogen, q=2, 3 or 4, and p=1, 2, 3 or 4. The invention also relates to compounds which can be obtained using such a method, to the use thereof, and to a substrate which has an aluminium layer or a layer containing aluminium on one surface.

A production method by which a biarylphosphine useful as a Buchwald phosphine ligand can be obtained in high purity is provided through an industrially advantageous process. The production method of a biarylphosphine comprises a step A of reacting a lithiated product obtained through lithiation of a halogenated benzene derivative with a benzene derivative to obtain a biphenyl derivative, and a step B of the reacting the biphenyl derivative with a halogenated phosphine. In the step A, the charge molar ratio of the halogenated benzene derivative to the benzene derivative is preferably 1.0 to 5.0.

The invention relates to lithium alkyl aluminates according to the general formula Li[AlR.sub.4] and to a method for preparing same, starting from LiAlH.sub.4 and RLi in an aprotic solvent. The invention also relates to compounds according to the general formula Li[AlR.sub.4] which can be obtained using the claimed method, and to the use thereof. The invention also relates to the use of a lithium alkyl aluminate Li[AlR.sub.4] as a transfer reagent for transferring at least one radical R to an element halide or metal halide and to a method for transferring at least one radical R to a compound E(X).sub.q for preparing a compound according to the general formula E(X).sub.q-pR.sub.p, where E=aluminium, gallium, indium, thallium, germanium, tin, lead, antimony, bismuth, zinc, cadmium, mercury, or phosphorus, X=halogen, q=2, 3 or 4, and p=1, 2, 3 or 4. The invention also relates to compounds which can be obtained using such a method, to the use thereof, and to a substrate which has an aluminium layer or a layer containing aluminium on one surface.

The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect.

##STR00001##

A method for producing a phosphinobenzene borane derivative comprises a reaction step (A) of obtaining liquid A containing a 1,2-dihalogenobenzene represented by the following general formula (1):

##STR00001##

obtaining liquid B containing a phosphine borane compound obtained by deprotonating a hydrogen-phosphine borane compound represented by the following general formula (2):

##STR00002##

and then adding the liquid B to the liquid A to be allowed to react to thereby obtain the phosphinobenzene borane derivative represented by the following general formula (3):

##STR00003##

According to the present invention, there can be provided the industrially advantageous method for producing the phosphinobenzene borane derivative.

The present invention relates to a ligand compound, a catalyst system for olefin oligomerization and a method for oligomerizing an olefin using same. The catalyst system for olefin oligomerization according to the present invention exhibits high selectivity to 1-hexene or 1-octene while having excellent catalytic activity, thus enabling more efficient preparation of alpha-olefins.

The present invention relates to a ligand compound, a catalyst system for olefin oligomerization and a method for oligomerizing an olefin using same. The catalyst system for olefin oligomerization according to the present invention exhibits high selectivity to 1-hexene or 1-octene while having excellent catalytic activity, thus enabling more efficient preparation of alpha-olefins.

The present invention relates to a ligand compound, a catalyst system for olefin oligomerization and a method for oligomerizing an olefin using same. The catalyst system for olefin oligomerization according to the present invention exhibits high selectivity to 1-hexene or 1-octene while having excellent catalytic activity, thus enabling more efficient preparation of alpha-olefins.