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Transition-Metal-Free Defluorosilylation of Fluoroalkenes with Silylboronates
Release time:2019-08-16    clicks:785

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 play a key role in the construction of natural products, pharmaceuticals, and manmade materials. Converting the normally highly stable fluoroalkenes into silylated fluoroalkenes by selective defluorosilylation is a challenging task. Herein, we report a simple, inexpensive and robust defluorosilylation of a variety of fluoroalkenes with silylboronates in the presence of alkoxy base to directly synthesize various silylated fluoroalkenes. The protocol features mild and safe reaction conditions that avoid a catalyst, a transition metal, a ligand, and high reaction temperature and tolerates a wide scope of fluoroalkene substrates without compromising the efficiency. Density functional theory calculations show that transient silyl anion complex undergoes an SN2’ or SN V substitution, which is responsible for this base-mediated defluorosilylation.