Alkyne aminohalogenation enabled by DBU-activated N-haloimides: direct synthesis of halogenated enamines.
نویسندگان
چکیده
Activated by DBU, N-haloimides can be used as both halogen and nitrogen sources to achieve the difunctionalization of terminal alkynes, giving rise to useful halogenated enamines with high efficiency and high regio- and stereoselectivities. The cascade reaction features simple manipulation, mild conditions, a broad substrate scope, readily available reagents, and atom-economy.
منابع مشابه
The stereoselective formation of bicyclic enamines with bridgehead unsaturation via tandem C-H bond activation/alkenylation/electrocyclization.
Bridgehead bicyclic unsaturated enamines were prepared by a tandem rhodium-catalyzed C-H bondactivation/alkenylation/electrocyclization of alkyne-tethered unsaturated imines. These strained bicyclic enamines exhibitunique reactivity: for example, they give N-Alkylated products upon treatment with alkylating reagents and undergo doublebond isomerization to alleviate ring strain upon ...
متن کاملSilver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
A silver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN3 is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of β-sulfonyl enamines without electron-withdrawing ...
متن کاملNickel-catalyzed alkyne annulation by anilines: versatile indole synthesis by C-H/N-H functionalization.
Versatile nickel catalysts enabled the step-economical synthesis of decorated indoles through alkyne annulations with anilines bearing removable directing groups. The C-H/N-H activation strategy efficiently occurred in the absence of any metal oxidants and with excellent selectivities.
متن کاملFormal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy
An iron(II)-mediated aminohalogenation of a cyclopentenyl N-tosyloxycarbamate provided new access to the key intermediate for the synthesis of (-)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N-iron...
متن کاملHalogenated Graphdiyne and Graphyne Single Layers: A Systematic Study
Graphyne and graphdiyne families of flat carbon (sp2/sp) networks with high degrees of π-conjunction are attracting much attention due to their promising electronic, optical, and mechanical properties. In the present investigation we have studied the structural, mechanical, electrical and optical properties of halogenated graphdiyne and graphyne. The optical spectra of pure and halog...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical communications
دوره 50 18 شماره
صفحات -
تاریخ انتشار 2014