中文摘要 本篇以亞硝苯 (nitrosobenzene) 與四氟硼酸亞硝鎓 (nitrosonium tetrafluoroborate) 在酸性條件下對苄基碳進行氧化反應生成芳基酮 (aryl ketones) 及芳基醛 (aryl aldehydes)，並研究其反應機制。四氟硼 酸亞硝鎓在酸性條件下會釋出 NO+ (nitrosonium ion)，藉由 (NO+, nitrosonium ion) 與亞硝苯 (nitrosobenzene) 形成的錯合物，進行苄基 氫擷取反應 (benzylic hydrogen abstraction) 後生成次硝酸 (HNO, nitroxyl / azanone) 與苄自由基 (benzylic radical)，再與亞硝苯陽離子 結合並去質子後得到氧化亞胺 (imine oxide)，經水解後得到芳基酮。 此方法條件溫和且反應試劑容易取得，我們利用此方法製備出 21 種芳基酮與 4 種芳基醛，最高產率可達 99 %，期望此方法未來 可以被經常應用在此氧化領域中。;Abstract In this study, we report the oxidation of benzylic carbons using nitrosobenzene and nitrosonium tetrafluoroborate (NOBF4) under acidic conditions to afford aryl ketones and aryl aldehydes. The reaction mechanism was also investigated. Under acidic conditions, NOBF4 generates the nitrosonium ion (NO+), which forms a complex with nitrosobenzene. This complex facilitates benzylic hydrogen abstraction, leading to the formation of nitroxyl (HNO, also known as azanone or nitroxyl) and a benzylic radical. Subsequent coupling of the benzylic radical with the nitrosobenzene-derived cation, followed by deprotonation, affords an imine oxide intermediate, which undergoes hydrolysis to yield the corresponding aryl ketone. This method features mild reaction conditions and employs readily available reagents. Using this protocol, we successfully synthesized 21 aryl ketones and 4 aryl aldehydes with yields of up to 99 %. We anticipate that this method will find broad application in the field of benzylic oxidation chemistry
