jo5b01684_si_002.cif (17.87 kB)
Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides
datasetposted on 2015-09-18, 00:00 authored by Zheng Yang, Wen-Juan Hao, Shu-Liang Wang, Jin-Peng Zhang, Bo Jiang, Guigen Li, Shu-Jiang Tu
A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C–O, C–N, and N–S bond cleavage, and C–S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.
TBHPpresencereaction timesulfonohydrazideregioselectivitygroup compatibilityvarietyHOAcPropargyl Alcoholsallenyl sulfonesMechanistic studiesSynthesiSulfonyl HydrazidesAsequentialsulfonyl hydrazidesreagentsulfonohylation proceedsyieldtransformationpropargyl alcoholsAllenyl Sulfonescleavageformationbond