Electrochemical vicinal oxyazidation of α-arylvinyl acetates

• Yi-Lun Li,
• Zhaojiang Shi,
• Tao Shen and
• Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

• diverse α-azidoketones in good yields without the use of a stoichiometric amount of chemical oxidant. A range of functionality is shown to be compatible with this transformation, and further applications are demonstrated. Keywords: azide; azidoketone; electrosynthesis; enol acetate; radical

• diverse organic frameworks. Herein, we report that the electrochemical oxyfunctionalization strategy could be well applied to the synthesis of α-azidoketone using readily available α-arylvinyl acetates, and azidotrimethylsilane (Scheme 1C). Results and Discussion The constant cell potential electrolysis

• (Ecell = 2.3 V, carbon cloth anode, and Pt cathode) of 1-phenylvinyl acetate (1) with azidotrimethylsilane was performed and the desired α-azidoketone (2) was obtained in 68% yield (Table 1, entry 1, for details of the reaction optimization see Supporting Information File 1). The cyclic voltammetry

Synthesis of crispine A analogues via an intramolecular Schmidt reaction

• Ajoy Kapat,
• Ponminor Senthil Kumar and
• Sundarababu Baskaran

Beilstein J. Org. Chem. 2007, 3, No. 49, doi:10.1186/1860-5397-3-49

• with aryl migration rather than alkyl migration resulting in the formation of benzo[e]indolizidine [A] as a major product (Scheme 3).[29] In this communication, we report the synthesis of crispine A analogues (2–5) using an intramolecular Schmidt reaction of azidoketone 6 as a key step. The azidoketone