95188-18-4Relevant academic research and scientific papers
Regioselective Vinylation of Remote Unactivated C(sp3)?H Bonds: Access to Complex Fluoroalkylated Alkenes
Wu, Shuo,Wu, Xinxin,Wang, Dongping,Zhu, Chen
, p. 1499 - 1503 (2019/01/04)
Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C?H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp3)?H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp3)?H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp3)?H bonds. The remote C(sp3)?H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.
NADH MODELS-19 CYCLOPROPANE RING AS A CHEMICAL PROBE IN THE STUDY OF THE MECHANISM OF HYDROGEN TRANSFER BY 1,4-DIHYDROPYRIDINE DERIVATIVES
Meijer, Louis H. P.,van Niel, Johannes C. G.,Pandit, Upendra K.
, p. 5185 - 5196 (2007/10/02)
N-(Cyclopropylmethylene)phenylamines (1a-c), cyclopropyl 2-pyridyl ketones (5a-c) and ethyl cyclopropylmethylenepyruvate (14) have been subjected to reduction by 1,4-dihydropyridines in the presence of magnesium ions, and by tin hydrides.The reactions with 1,4-dihydropyridines do not involve cleavage of the three-membered ring in the reduction step.The observed acyclic product from 2-pyridyl 2,2-dimethylcyclopropyl ketone (5b) is a consequence of ring cleavage prior to reduction of the carbonyl function.In contrast, reduction of 1a-c and 5a-c by tin hydrides leads to products in which the cyclopropane moiety has undergone ring-opening.These findings support a hydride transfer mechanism for reductions with NADH models.
