1,3 -双 極 子 と し て の 性 質 を 崩 し て展 開 す る 有 機 ア ジ ド の 合 成 化 学

Organic azides are well-known for the synthetic organic reactions by their energetic characteristics and the click functionality connecting two components. Especially in click chemistry, the azido groups as 1,3-dipolar play a key role in chemical biology. On the other hand, azido groups can also work as nucleophiles possessing diazonium leaving groups and as electrophiles, but the ^low 1,3-dipolar ^reactivity use ^has of ^avoided organic azides. ^{their use.} As ^Herein, nucleophiles, ^{we disclose} the organic ^{our synthetic} azides with ^achievements allyl／propargyl ^{in the} cations ^non- and sulfonium ions gave the appropriate products, including C-C bond migration. We also demonstrated that the intramolecular hydrogen bonding interaction promoted the electrophilicity and suppressed the nucleophilicity of the azides to achieve site-selective conjugation. Furthermore, β - elimination followed by condensation converted the azido groups at the carbonyl α -position to the different click functional groups. This site-selective azido group conversion enabled the undistinguishable triazide molecule to the distinguishable triple-click scaffold compound possessing three different click groups.