TY - JOUR
T1 - Environmentally Benign and User-Friendly in Situ Generation of Nitrile Imines from Hydrazones for 1,3-Dipolar Cycloaddition
AU - Song, Liyan
AU - Lai, Yunrong
AU - Li, Hongzuo
AU - Ding, Jipeng
AU - Yao, Hongliang
AU - Su, Qian
AU - Huang, Binbin
AU - Ouyang, Ming An
AU - Tong, Rongbiao
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/8/5
Y1 - 2022/8/5
N2 - Nitrile imines are highly reactive and versatile dipoles and conventionally generated in situ from unstable hydrazonyl halides under basic conditions. Herein, we report the first green and user-friendly protocol for in situ generation of nitrile imines from Oxone-KBr oxidation of hydrazones and base-promoted dehydrobromination. The nitrile imines were demonstrated for 1,3-dipolar cycloaddition with various dipolarophiles, including alkene and alkyne groups. With its green nature, ease of operation, and air and moisture tolerance, we expect our method will find wide applications in organic synthesis.
AB - Nitrile imines are highly reactive and versatile dipoles and conventionally generated in situ from unstable hydrazonyl halides under basic conditions. Herein, we report the first green and user-friendly protocol for in situ generation of nitrile imines from Oxone-KBr oxidation of hydrazones and base-promoted dehydrobromination. The nitrile imines were demonstrated for 1,3-dipolar cycloaddition with various dipolarophiles, including alkene and alkyne groups. With its green nature, ease of operation, and air and moisture tolerance, we expect our method will find wide applications in organic synthesis.
UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000887032700001
UR - https://openalex.org/W4286716448
UR - https://www.scopus.com/pages/publications/85135920067
U2 - 10.1021/acs.joc.2c01391
DO - 10.1021/acs.joc.2c01391
M3 - Journal Article
SN - 0022-3263
VL - 87
SP - 10550
EP - 10554
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -