Catalytic boronate ester synthesis from boron reagents and hydrocarbons

Assignee: Board of Trustees of Michigan State University

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Quick Facts

Patent No.: US 6,878,830
App. No.: 10/194,809
Granted: Apr 12, 2005
Kind: B2

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Abstract

A process for producing a ring-substituted arene borane which comprises reacting a ring-substituted arene with an HB organic compound in the presence of a catalytically effective amount of an iridium or rhodium complex with three or more substituents, excluding hydrogen, bonded to the iridium or rhodium and a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium, to form the ring-substituted arene borane. Also provided are catalytic compounds for catalyzing the process comprising an iridium or rhodium complex with three or substituents, excluding hydrogen, bonded to the iridium or rhodium and optionally, a phosphorus organic ligand, which is at least in part bonded to the iridium or rhodium.

Claims (50)

1. A catalytic composition comprising:

an iridium complex of the formula: (BY) n —Ir-(ligand) m with three or more n and m substituents, excluding hydrogen, bonded to the iridium BY is a boron moiety and the ligand is selected from the group consisting of a phosphorus organic ligand, an organic amine, an imine, a nitrogen heterocycle, and an ether wherein the ligand is at least in part bonded to the iridium.

2. The catalytic composition of claim 1 wherein the phosphorus organic ligand is selected from the group consisting of trimethyl phosphine (PMe 3 ), 1,2-bis(dimethylphosphino)ethane (dmpe), and 1,2-bis(diphenylphosphino)ethane (dppe).

3. The catalytic composition of claim 1 wherein the iridium complex is (ArH)Ir(BY) 3 wherein ArH is selected from the group consisting of aromatic, heteroaromatic, polyaromatic, and heteropolyaromatic hydrocarbon; and BY is a boron moiety of the formula

4. The catalytic composition of claim 1 wherein the iridium complex is (MesH)Ir(BY) 3 wherein MesH is mesitylene; and BY is a boron moiety selected from the group consisting of

5. The catalytic composition of claim 1 wherein the iridium complex is (P(Y 4 )(Y 5 )(Y 6 )) 3 Ir (H) n (BY) 3-n wherein Y 4 , Y 5 , and Y 6 are each selected from the group consisting of hydrogen, halide, alkyl, aryl, alkoxide (—O(R 11 )), and amide (—N(R 12 )(R 13 )) wherein R 11 , R 12 , and R 13 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; n is 0, 1, or 2; and BY is a boron moiety selected from the group consisting of

6. The catalytic composition of claim 1 wherein the iridium complex is (P(R 14 )(R 15 )(R 16 )) 3 Ir (H) n (BY) 3-n wherein R 11 , R 12 , and R 13 are each selected from the group consisting of hydrogen, linear alkyl, branched alkyl, and a carbon in a cyclic structure; n is 0, 1, or 2; and BY is a boron moiety selected from the group consisting of

7. The catalytic composition of claim 1 wherein the iridium complex is (P(Y 4 )(Y 5 )(Y 6 )) 3 Ir (H)(R 17 )(BY) wherein Y 4 , Y 5 , and Y 6 are each selected from the group consisting of hydrogen, halide, alkyl, aryl, alkoxide (—O(R 11 )), and amide (—N(R 12 )(R 13 )) wherein R 11 , R 12 , and R 13 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; R 17 is selected from the group consisting of a linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, aryl, and a carbon in a cyclic structure; and BY is a boron moiety selected from the group consisting of

8. The catalytic composition of claim 1 wherein the iridium complex is (P(R 14 )(R 15 )(R 16 )) 3 Ir (H)(R 17 )(BY) wherein R 14 , R 15 , and R 16 are each selected from the group consisting of hydrogen, linear alkyl, branched alkyl, and a carbon in a cyclic structure; R 17 is selected from the group consisting of a linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, aryl, and a carbon in a cyclic structure; and BY is a boron moiety selected from the group consisting of

9. The catalytic composition of claim 1 wherein the iridium complex is {(PY 7 P)Ir(BY) 3 } 2 (μ 2 -(PY 7 P)) wherein BY is a boron moiety selected from the group consisting of

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; (PY 7 P) is R 18 R 19 P—Y 7 —PR 20 R 21 wherein R 18 , R 19 , R 20 , and R 21 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure, and Y 7 is a chain containing 1 to 12 carbons.

10. The catalytic composition of claim 1 wherein the iridium complex is (PY 7 P)(P(Y 4 )(Y 5 )(Y 6 ))Ir(BY) 3 wherein BY is a boron moiety selected from the group consisting of

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; Y 4 , Y 5 , and Y 6 are each selected from the group consisting of hydrogen, halide, alkyl, aryl, alkoxide (—O(R 11 )), and amide (—N(R 12 )(R 13 )) wherein R 11 , R 12 , and R 13 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; and (PY 7 P) is R 18 R 19 P—Y 7 —PR 20 R 21 wherein R 18 , R 19 , R 20 , and R 21 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure, and Y 7 is a chain containing 1 to 12 carbons.

11. The catalytic composition of claim 1 wherein the iridium complex is (PY 7 P)(P(R 14 )(R 15 )(R 16 ))Ir(BY) 3 wherein BY is a boron moiety selected from the group consisting of

wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure; R 14 , R 15 , and R 16 are each selected from the group consisting of hydrogen, linear alkyl, branched alkyl, and a carbon in a cyclic structure; (PY 7 P) is R 18 R 19 P—Y 7 —PR 20 R 21 wherein R 18 , R 19 , R 20 , and R 21 are each selected from the group consisting of hydrogen, linear alkyl containing 1 to 8 carbon atoms, branched alkyl containing 1 to 8 carbons, and a carbon in a cyclic structure, and Y 7 is a chain containing 1 to 12 carbons.

12. The catalytic composition of claim 1 wherein the iridium complex is {(PP)Ir(BY) 3 } 2 (μ 2 -(PP)) wherein BY is a boron moiety selected from the group consisting of