| US 7,514,563 B2 | ||
| Process for producing cyano substituted arene boranes and compounds | ||
| Milton R. Smith, III, East Lansing, Mich. (US); Robert E. Maleczka, DeWitt, Mich. (US); and Ghayoor A. Chotana, East Lansing, Mich. (US) | ||
| Assigned to Board of Trustees of Michigan State University, East Lansing, Mich. (US) | ||
| Filed on Jun. 08, 2006, as Appl. No. 11/449,280. | ||
| Claims priority of provisional application 60/689161, filed on Jun. 09, 2005. | ||
| Prior Publication US 2006/0281939 A1, Dec. 14, 2006 | ||
| Int. Cl. C07D 207/30 (2006.01); C07D 211/78 (2006.01); C07D 323/02 (2006.01); C07C 255/51 (2006.01); C07F 5/02 (2006.01) | ||
| U.S. Cl. 546—286 [546/287; 549/4; 549/5; 549/213; 558/419; 558/442; 568/2; 568/6] | 17 Claims |
| 1. A process for producing a cyano ring-substituted arene borane wherein the arene is selected from the group consisting of
pyridine, pyrrole, furan, thiophene and benzene, the process comprising:
reacting a ring-substituted cyano arene with an HB or a B—B organic compound, in the presence of a catalytically effective
amount of a catalytic composition comprising an iridium complex and an organic ligand at least in part bonded to the iridium
complex, the organic ligand being selected from the group consisting of a phosphorus organic ligand, an organic amine, an
imine, and a nitrogen-substituent organic ligand comprising at least one 5- or 6-membered nitrogen heterocycle to form the
cyano ring-substituted arene borane;
wherein:
(i) the iridium complex is selected from the group consisting of (Cp*)Ir(H)2(Me3P), (Cp*)Ir(H)(BPin)(Me3P), (CP*)Ir(H)(C6H5)(Me3P), (Ind)Ir(COD), (MesH)Ir(BPin)(B(OR)2), ((R1)3P)3Ir(B(OR2)2)3, (R1)2P)2Ir(BPin)3, [((R1)2P)3Ir((R2O)2B)3]2, ((R1)3P)4Ir(BPin), ((R1)2P)2Ir(BPin)3, (MesH)Ir(BPin)3, IrCl(COD), [IrCl(COD)]2, [Ir(OMe)(COD)]2, and combinations thereof; and
(ii) in the iridium complex, CP* is 1,2,3,4,5-methylcyclopentadienyl, BPin is pinacolborane, Me is methyl, H is hydrogen,
P is phosphorus, Ind is indenyl, COD is 1,5-cyclooctadiene, MesH is mesitylene, and R, R1, and R2 are each selected from the group consisting of hydrogen, linear or branched alkyl containing 1 to 8 carbons, aryl, and a carbon
in a cyclic structure.
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