The formation of carbon (sp3) – carbon (sp3) bonds is an important area of interest among synthetic chemists. A major limitation of known methods of this coupling is β-hydride elimination, which results in numerous side products instead of the desired product. Using hypervalent iodine and metalloids presents a novel method of obtaining a product with carbon (sp3) – carbon (sp3) bonding. The reaction, termed HIGES (Hypervalent Iodine Guided Electrophilic Substitution), involves the synthesis of a highly reactive alkylated hypervalent iodine intermediate. A transmetalation step results in the hypervalent iodine intermediate acting as a guide in selective electrophilic aromatic substitution. The mechanism for this transformation is thought to proceed through a Berry pseudorotation. This methodology exploits the hypervalent nature of iodine and the development of the HIGES reaction can prove to be very beneficial to the synthetic community.

Development of hypervalent iodine guided electrophilic substitution (HIGES) reactions

255th National Meeting (2018)

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