System for controlling the reactivity of boronic acids
AssigneeThe Board of Trustees of the University of Illinois
InventorsMartin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
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Abstract
A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.
Claims24
A method of performing a chemical reaction, comprising:
- contacting a protected organoboronic acid with a reagent,
- the protected organoboronic acid comprising a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond;
- wherein the protected organoboronic acid is represented by formula (X):
- R10represents the organic group,
- B represents the boron having sp3 hybridization, and
- R20, R21, R22, R23 and R24 independently are selected from the group consisting of hydrogen and an organic group,
- where R10 is chemically transformed, and
- the boron is not chemically transformed.
A method of performing a chemical reaction, comprising:
- contacting a protected organoboronic acid and organohalide with palladium catalyst, in the presence of aqueous base;
- the protected organoboronic acid comprising a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond;
- wherein the protected organoboronic acid is represented by formula (X):
- R10 represents the organic group,
- B represents the boron having sp3 hybridization, and
- R20, R21, R22, R23 and R24 independently are selected from the group consisting of hydrogen and an organic group,
- to provide a cross-coupled product comprising R10.
A method of performing a chemical reaction, comprising:
- contacting a first organoboronic acid and a first organohalide with a palladium catalyst, to provide a first cross-coupled product;
- the first organohalide comprising a first boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the first boron, and a first organic group, substituted with halide, bonded to the first boron through a boron-carbon bond, wherein the first organohalide is represented by formula (X):
- R10 represents the first organic group, substituted with halide,
- B represents the first boron having sp3 hybridization, and
- R20, R21, R22, R23 and R24 independently are selected from the group consisting of hydrogen and an organic group, and
- the first cross-coupled product comprising the first boron having sp3 hybridization, the conformationally rigid protecting group bonded to the first boron, and a second organic group, different from the first organic group, bonded to the first boron through a boron-carbon bond;
- removing the conformationally rigid protecting group from the first boron to form a second organoboronic acid, and
- contacting the second organoboronic acid and a second organohalide with a palladium catalyst, to provide a second cross-coupled product.
Dependencies are inferred from the claim text.