1,2‐Bis‐Triazenylarenes Enable Vicinal Sandmeyer‐Type Reactions
Year: 2025
Type: article
Abstract: The introduction of two nucleophiles in the vicinal position of arenes via Sandmeyer‐type reactions is compromised by the problematic diazotization of ortho‐diaminoarenes. Herein, it is shown that vicinal substitution reactions are facilitated by the use of 1,2‐bis‐triazenylarenes. Two distinct methodologies for the synthesis of these triazenes are presented. The first approach involves the sequential conversion of 1‐amino‐2‐iodoarenes into first mono‐ and then bis‐triazenylarenes. The second procedure is based on Ru‐catalyzed [2 + 2 + 2] cycloaddition reactions between diynes and a 1,2‐bis‐triazenylalkyne. The two triazene groups in the products can be substituted sequentially by a range of nucleophiles including fluoride, chloride, bromide, iodide, azide, hydroxide, methoxide, and acetamide.
Source: Angewandte Chemie
Institution: École Polytechnique Fédérale de Lausanne
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,790
OpenAlex ID: W4408320453