Tunable Functionalization of Saturated C–C and C–H Bonds of N,N′-Diarylpiperazines Enabled by tert-Butyl Nitrite (TBN) and NaNO2 Systems

• DOI: 10.1021/acs.orglett.9b01574
• Publication Date: 2019-06-25T19:42:34Z
• Authors: Kaixuan He; Ting Zhang; Shuwei Zhang; Zheng Sun; Yuxian Zhang; Yu Yuan; Xiaodong Jia
• Keywords: Surface Modification

A tunable functionalization of saturated C–C and C–H bonds N,N′-diarylpiperazine derivatives was realized by tert-butyl nitrite (TBN) NaNO2 systems, respectively. When TBN employed as the oxidant, bond cleavage occurred smoothly, providing a series formamides in good yields. In presence NaNO2, oxidation achieved, resulting efficient synthesis nitroalkenes. The mechanistic study shows that mixed mechanism is involved these reactions, which generated enamine might be key intermediate.