Catalysis using phosphine oxide compounds
AssigneeE. I. Du Pont de Nemours and Company
InventorGeorge Yanwu Li
Life of this patent
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Abstract
Phosphine oxide compounds were used with transition metals, preferably palladium and nickel, to produce biaryls and arylamines via cross-coupling reactions with aryl halides and arylboronic acids, aryl Grignard reagents or amines.
Claims8
A process to prepare biaryls of the formula R1-R7 comprising contacting a Grignard reagent of the formula R7—MgX with an aryl compound of the formula R1—X in the presence of a catalytic amount of a coordination compound comprising one or more transition metals complexed to a phosphine oxide compound of the formula HP(O)R4R5,
- wherein X is a halogen;
- R1 is an optionally substituted aryl;
- R7 is selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, hydrocarbylamino, alkoxy, aryloxy, and heterocyclic;
- and
- R4 and R5 are independently selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, heterocyclic, organometallic, Cl, Br, I, SQ1, OQ2, PQ3Q4, and NQ5Q6, where Q1, Q2, Q3, Q4, Q5, and Q6 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, hydrocarbylamino, alkoxy, aryloxy, and heterocyclic, and optionally R4 and R5 can together form a ring.
A method for the use of phosphine oxides as ligands for homogeneous catalysis biaryls of the formula R1-R7 comprising:
- (1) preparing a coordination compound comprising one or more transition metals complexed to a phosphine oxide compound of the formula HP(O)R4R5,
- wherein X is a halogen;
- R1 is an optionally substituted aryl;
- R7 is selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, hydrocarbylamino, alkoxy, aryloxy, and heterocyclic;
- and
- R4 and R5 are independently selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, heterocyclic, organometallic, Cl, Br, I, SQ1, OQ2, PQ3Q4, and NQ5Q6, where Q1, Q2, Q3, Q4, Q5, and Q6 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, hydrocarbylamino, alkoxy, aryloxy, and heterocyclic, and optionally R4 and R5 can together form a ring;
- and
- 2) contacting either a Grignard reagent of the formula R7—MgX with an aryl compound of the formula R1—X in the presence of a catalytic amount of the coordination compound prepared in step (1) to form biaryls of the formula R1-R7.
Dependencies are inferred from the claim text.