The formation of carbon (sp3) – carbon (sp3) bonds are of interest to the synthetic community. Due to β-hydride elimination, the formation of sp3 carbon-carbon bonds is difficult as various side reactions and products occur. The novel methods employed in this project use hypervalent iodine and a soft metal alkyl transfer reagent to create an unstable alkyl-hypervalent iodine intermediate that can then be treated with a hard metal alkyl group such as a Grignard reagent. The mechanism for such a transformation is thought to proceed through either an SN2-type reaction, the nucleophile attacking the carbon bonded to the hypervalent iodine; or a process where the hard metal alkyl group directly attacks the hypervalent iodine and the carbon-carbon bond forming step involves reductive elimination. The methodology presented will focus on the transmetallation of trifluoroborate substrates with hypervalent iodine.

Progress towards the cross-coupling of sp3 carbons using hypervalent iodine

254th National Meeting (2017)

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