正文

Copper-Facilitated Suzuki Reactions: Application to 2-Heterocycl

(2023-02-19 15:49:17) 下一個

Since the discovery of the palladium-catalyzed Suzuki Miyaura reaction, organoboronates have been developed as powerful reagents for carbon-carbon bond formation due to their stability, nontoxicity, and functional group compatibility. Although numerous ligand systems have been developed for a wide array of coupling partners, reaction of electron-deficient boronates such as 2-pyridyl remains challenging2 and of high interest to the synthetic community, particularly the pharmaceutical industry. For example, coupling of 2-pyridylboronic acid was unsuccessful under a very general Suzuki coupling system.

It is hypothesized that transmetalation from boron to palladium of electron-deficient 2-heterocyclic boronates is slow relative to protodeboronation, leading to poor conversions.

In 2009, Deng reported  the successful copper(I)-facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope; furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.

Org. Lett., Vol. 11, No. 2, 2009

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