Catalysis

Reactivity (psychology)

Alkylation

Palladium

Alkyl

Indole test

Inorganic chemistry

Physical chemistry

Alternative medicine

Combinatorial chemistry

Fluoride

Organic chemistry

Reductive elimination

Surface modification

Cyclopropanation

Medicine

Chemistry

Aryl

Elimination reaction

Pathology

Angewandte Chemie International Edition

A palladium catalyzed C-H functionalization and consecutive β-fluoride elimination reaction between indole heterocycles and fluorinated diazoalkanes is reported. This approach provides for the first time a facile method for the rapid synthesis of gem-difluoro olefins using fluorinated diazoalkanes under mild reaction conditions. Cyclopropanation products were obtained when N-arylated rather than N-alkylated indoles were applied in this reaction. Mechanistic studies reveal the importance of the β-fluoride elimination step in this transformation. This method presents a new concept for the simple and direct transfer of a 1-aryl-(2,2-difluorovinyl) group to access gem-difluoro olefins.

Synthesis of <i>gem</i>‐Difluoro Olefins through C−H Functionalization and β‐fluoride Elimination Reactions

Synthesis of gem‐Difluoro Olefins through C−H Functionalization and β‐fluoride Elimination Reactions