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Transition-Metal-Free Defluorosilylation of Fluoroalkenes with Silylboronates

Release time:2019-08-16    clicks:408

The group publishes a Transition-Metal-Free Defluorosilylation of Fluoroalkenes with Silylboronates on Chin. J. Chem. Congrats Gao!

ABSTRACT: Silylated fluoroalkenes are important synthetic intermediates with complementary reactivity, which playa key role in the construction of natural products, pharmaceuticals, and manmade materials. Converting the normally highly stable fluoroalkenes intosilylated fluoroalkenes by selective defluorosilylation is a challenging task. Herein, we report a simple, inexpensive and robust defluorosilylation of a varietyof fluoroalkenes with silylboronates in the presence of alkoxy base to directly synthesize various silylated fluoroalkenes. The protocol features mildand safe reaction conditions that avoid a catalyst, a transition metal, a ligand, and high reaction temperature and tolerates a wide scope of fluoroalkenesubstrates without compromising the efficiency. Density functional theory calculations show that transient silyl anion complex undergoes an SN2’ or SNVsubstitution, which is responsible for this base-mediated defluorosilylation.