128318-85-4Relevant academic research and scientific papers
One-pot sequential and cascade formation of triazoles via palladium catalysed azide capture-1,3-dipolar cycloaddition
Gardiner, Mihaly,Grigg, Ronald,Kordes, Markus,Sridharan, Visuvanathar,Vicker, Nigel
, p. 7729 - 7735 (2001)
The development of cascade and sequential processes comprising the formation of allylic azides, from aryl/heteroaryl/vinyl halides, allene and sodium azide, by palladium catalysed anion capture, and cyclisation-anion capture, followed by 1,3-dipolar cycloaddition gives rise to a variety of new triazoles in good yield.
PALLADIUM(0)-CATALYZED AZIDATION OF ALLYL ESTERS WITH TRIMETHYLSILYL AZIDE
Safi, M.,Fahrang, R.,Sinou, D.
, p. 527 - 530 (1990)
Palladium(0)-catalyzed reaction of allyl esters with trimethylsilyl azide gives, under anhydrous conditions, the corresponding allyl azides.
Highly selective hydrosilylation of equilibrating allylic azides
Liu, Ruzhang,Liu, Yongmei,Wang, Juan,Wei, Zhen,Xue, Huaiguo
, p. 5038 - 5041 (2020)
The Pt-catalyzed hydrosilylation of equilibrating allylic azides is reported. The reaction provides only one out of four possible hydrosilylation products in good yields and with very high chemoselectivity (alk-1-enevs.alk-2-ene), regioselectivity (linearvs.branched), and excellent functional group tolerance.
Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes
Zhu, Rong,Buchwald, Stephen L.
, p. 8069 - 8077 (2015)
A versatile method for the rapid synthesis of diverse enantiomerically enriched lactones has been developed based on Cu-catalyzed enantioselective radical oxyfunctionalization of alkenes. The scope of this strategy encompasses a series of enantioselective difunctionalization reactions: oxyazidation, oxysulfonylation, oxyarylation, diacyloxylation, and oxyalkylation. These reactions provide straightforward access to a wide range of useful chiral lactone building blocks containing tetrasubstituted stereogenic centers, which are hard to access traditionally. (Chemical Equation Presented).
Synthesis method of 3-azidopropylsilane
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, (2020/06/05)
The invention discloses a synthetic method of 3-azidopropylsilane, wherein the method comprises the steps: firstly, allyl azide is synthesized by allyl bromide, and because the allyl azide is easy togenerate [3,3] rearrangement reaction at room temperatur
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
Solvent-dependent enantiodivergence in the chlorocyclization of unsaturated carbamates
Garzan, Atefeh,Jaganathan, Arvind,Salehi Marzijarani, Nastaran,Yousefi, Roozbeh,Whitehead, Daniel C.,Jackson, James E.,Borhan, Babak
, p. 9015 - 9021 (2013/07/26)
A remarkable solvent-controlled enantiodivergence is seen in the hydroquinidine 1,4-phthalazinediyl diether ((DHQD)2PHAL)-catalyzed chlorocyclization of unsaturated carbamates. Eyring plot analyses of this previously unreported reaction are used to probe and compare the R- and S-selective pathways. In the CHCl3/hexanes solvent system, the pro-R process shows a surprising increase in selectivity with increasing temperature. These studies point to a strongly solvent-dependent entropy-enthalpy balance between the pro-R and pro-S pathways. Two solvents, two enantiomers: Enantiodivergent hydroquinidine 1,4-phthalazinediyl diether ((DHQD) 2PHAL)-catalyzed chlorocyclization of unsaturated carbamates, controlled solely by the choice of solvent, yields oxazolidinones in high enantioselectivity (see scheme; DCDMH=1,3-dichloro-5,5-dimethyl hydantoin). The origin of the observed enantiodivergence is traced back to a solvent-selected entropy-enthalpy balance between pro-R and pro-S pathways that dictates the course of the reaction. Copyright
