65127-72-2Relevant articles and documents
Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles
Tian, Xianhai,Song, Lina,Rudolph, Matthias,Rominger, Frank,Oeser, Thomas,Hashmi, A. Stephen K.
supporting information, p. 3589 - 3593 (2019/02/09)
We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α-imino gold carbenes by N?S cleavage of sulfilimines. These gold carbenes undergo C?H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3-azabicyclo[3.1.0]hexan-2-imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold-catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza-heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α-imino gold carbenes. Moreover, an unexpected synthesis of 4-acylquinolines (3 examples) from 2-acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2-hydride shift onto the α-imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered.
Facile and efficient synthesis of 1-haloalkynes via DBU-mediated reaction of terminal alkynes and N-haloimides under mild conditions
Li, Mengru,Li, Yueju,Zhao, Baozhong,Liang, Fushun,Jin, Long-Yi
, p. 30046 - 30049 (2014/08/05)
Directly from terminal alkynes and with N-halosuccinimides (halo = Br and I) or N-cholorophthalimide as the halogen sources, DBU as the activator, 1-haloalkynes were prepared in good to excellent yields at room temperature. Bis(bromoalkyne) and bis(iodoal
Palladium-catalyzed bromoalkynylation of C-C double bonds: Ring-structure-dependent synthesis of 7-alkynyl norbornanes and cyclobutenyl halides
Li, Yibiao,Liu, Xiaohang,Jiang, Huanfeng,Liu, Bifu,Chen, Zhengwang,Zhou, Peng
supporting information; experimental part, p. 6341 - 6345 (2011/09/13)
Strain versus flexibility: The palladium-catalyzed reaction of haloalkynes with norbornene derivatives leads to 7-alkynyl norbornane products (see scheme). Key to the success of this reaction is the formation of a "bridging" palladium species, which can rearrange to result in a C-7 functionalization. The ring-structure-dependent [2+2] cycloaddition of haloalkynes with cyclooctene has been achieved in moderate to good yields under similar conditions. Copyright