System for controlling the reactivity of boronic acids

C - Chemistry – Metallurgy – 07 – D

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C07D 307/80 (2006.01) C07F 5/02 (2006.01)

Patent

CA 2694068

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. The compounds are preferably boronic acids protected with trivalent N- methyliminodiacetic acid ligands. The compounds can be used, for example, as reagents in Suzuki-Miyaura coupling reactions.

L'invention porte sur un acide organo-boronique protégé qui comprend un bore ayant une hybridation sp3, un groupe protecteur conformationnellement rigide, lié au bore, et un groupe organique lié au bore par une liaison bore-carbone. L'invention porte sur un procédé de réalisation d'une réaction chimique qui comprend la mise en contact d'un acide organo-boronique protégé avec un réactif, l'acide organo-boronique protégé comprenant un bore ayant une hybridation sp3, un groupe protecteur conformationnellement rigide lié au bore, et un groupe organique lié au bore par une liaison bore-carbone. Le groupe organique est chimiquement transformé, et le bore n'est pas chimiquement transformé. Les composés sont, de préférence, des acides boroniques protégés par des ligands de type acide N-méthyliminodiacétique trivalents. Les composés peuvent être utilisés, par exemple, comme réactifs dans des réactions de couplage de Suzuki-Miyaura.

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