Carboazidation of Terminal Alkenes with Trimethylsilyl Azide and Cyclic Ethers Catalyzed by Copper Powder under Oxidative Conditions

Abstract

Copper-catalyzed carboazidation of alkenes with trimethylsilyl azide and cyclic ethers has been achieved. The employment of naturally abundant copper catalysts allowed cyclic ethers to be used as alkylating reagents under oxidative conditions. The use of styrene derivatives and 1,1-diaryl alkenes afforded carboazidation products. In addition, application of five-and six-membered cyclic ethers to the present reaction gave target organic molecules bearing azide and cyclic ether groups with perfect regioselectivity. Radical trapping and clock experiments revealed that the present reaction proceeded via the radical pathway. To further demonstrate the utility of this carboazidation reaction, transformations from the azide group to the related nitrogen-containing compounds were also performed.

Copper‐Catalyzed Diazidation of Allenes: Access to 3‐(Azidomethyl)‐2H‐Azirines

“…Based on the above experimental results and relevant reports, [15] a possible mechanism is proposed in Scheme 5. To begin with, Cu(II)(OH) A is generated through a single electron transfer (SET) process involving a copper(I) catalyst and tert-butyl hydrogen Scheme 3.…”