Reductive Iodonium: Teaching an Old Claisen New Tricks

The drive to discover new transformations that enable C–C bond formation remains at the heart of challenges in contemporary organic synthesis. This is crucial for the expansion of the synthetic toolbox, providing the chemist with original ways to assemble a desired target – be it a natural product or a manmade compound. Many industries rely heavily on novel approaches in organic synthesis to develop new medicines, agrochemicals, polymer monomers, or fragrances in ever-more environmentally friendly and economical ways.

[1]  Sarah E. Wengryniuk,et al.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents. , 2019, Journal of the American Chemical Society.

[2]  Zhi‐Xiang Wang,et al.  The ortho-Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect. , 2019, Angewandte Chemie.

[3]  Xueliang Huang,et al.  Sulfoxide-mediated α-arylation of carbonyl compounds. , 2011, Journal of the American Chemical Society.

[4]  B. Olofsson,et al.  Diaryliodonium salts: a journey from obscurity to fame. , 2009, Angewandte Chemie.

[5]  Ana M. Martin Castro,et al.  Claisen rearrangement over the past nine decades. , 2004 .

[6]  Phillip K. Koech,et al.  Phosphine catalyzed alpha-arylation of enones and enals using hypervalent bismuth reagents: regiospecific enolate arylation via nucleophilic catalysis. , 2004, Journal of the American Chemical Society.

[7]  R. Sebastián,et al.  An alternative to the classical α-arylation: the transfer of an intact 2-iodoaryl from ArI(O₂CCF₃)₂. , 2014, Angewandte Chemie.

[8]  E. Negishi.  Novel and selective α-substitution of ketones and other carbonyl compounds based on Pd-catalyzed cross coupling of α,β-unsaturated carbonyl derivatives containing α-halogen or α-metal groups ☆ , 1999 .

[9]  M. D. Hill,et al.  Applications of Fluorine in Medicinal Chemistry. , 2015, Journal of medicinal chemistry.

[10]  E. Martín,et al.  Hypervalent Activation as a Key Step for Dehydrogenative ortho C-C Coupling of Iodoarenes. , 2015, Chemistry.