Cuh mediated hydroamination of styrene

cuh mediated hydroamination of styrene Excellent yields and enantioselectivities since then, cuh-catalyzed hydroamination has been extended to a wide scope of substrate classes, including vinyl silanes, terminal alkenes, internal unactivated alkenes, alkynes, and strained cyclic alkenes7,8 a general catalytic cycle for the hydroamination of styrene is shown in scheme 1.

Enantioselective copper(i) hydride (cuh)-catalyzed hydroamination has undergone significant development over the past several years in order to gain a general understanding of the factors governing these reactions, kinetic and spectroscopic studies were performed on the cuh-catalyzed hydroamination of styrene. A detailed computational exploration of mechanistic intricacies of the copper(i) hydride (cuh)-catalysed hydroamination of styrene with a prototype hydroxylamine ester by a recently reported. Treatment of styrene and nitrogen source by pd(oac) 2 (5 mol%), bc (55 mol%) in isopropanol under aerobic condition failed to achieve hydroamination, and only trace alcohol oxidation product was detected.

cuh mediated hydroamination of styrene Excellent yields and enantioselectivities since then, cuh-catalyzed hydroamination has been extended to a wide scope of substrate classes, including vinyl silanes, terminal alkenes, internal unactivated alkenes, alkynes, and strained cyclic alkenes7,8 a general catalytic cycle for the hydroamination of styrene is shown in scheme 1.

Additionally,wemonitored the cuh-catalyzed hydro-amination of styrene using 2ain the presence or absence of tbuoh/pph3 through 1hnmr spectroscopyweobserved that the reaction rate was also significantly enhanced by the hydroamination of alkenes with arylamine o-benzoates for. Prior to the reports of cu-catalyzed hydroamination, an analogous aminoboration process was reported in which a styrene was converted to the 1,2-aminoboronate in the presence of b 2 pin 2 and a hydroxylamine o-benzoate reagent. A detailed computational exploration of mechanistic intricacies of the copper(i) hydride (cuh)-catalysed hydroamination of styrene with a prototype hydroxylamine ester by a recently reported [(dppbz)cuh] catalyst (dppbz={p^p}=1,2-bis(diphenylphosphino)-benzene) is presented.

Skip to main content. Scheme 7: intermolecular hydroamination between styrene 8 and amine 9 to afford anti-markovnikov product 10 using catalyst f 2 the substrate scope of f is rather limited, catalyzing reactions with only phenyl-substituted olefins or alkynes. Cuh-catalysed hydroamination of styrene with hydroxylamine esters: a coupled cluster scrutiny of mechanistic pathways. Kinetic and spectroscopic studies of the cuh-catalyzed hydroamination of styrene these studies have provided evidence that the phosphine-ligated cuobz complex 5 is the resting state of the catalyst and the turnover-limiting step entails regeneration of the cuh catalyst via its reaction with a.

Hydroamination of 1,1-disubstituted olefins as a practical and general method for the synthesis of β-chiral amines received: september 22, 2014 published: october 22, 2014 figure 1 (a) representative β-chiral amines (b) hydroamination strategy for their preparation figure 2 proposed mechanism of cuh-catalyzed anti-markovnikov hydroamination. In conclusion, we have developed a novel strategy for the palladium-catalyzed inter- and intramolecular hydroamination of styrenes that are coupled to alcohol oxidation under oxidative condition this reaction employs a nitrogen-based ligand and nfsi as the oxidant further study on the asymmetric hydroamination of styrene is in progress 3.

A sophisticated computational methodology was employed to contribute towards a more precise understanding of mechanistic intricacies and catalytic structure-reactivity relationships of cuh-mediated hydroamination of styrene with hydroxylamine esters.

Cuh mediated hydroamination of styrene

In 2015, buchwald extended the cuh-catalyzed hydroamination strategy to the direct enantioselective synthesis of secondary chiral amines (scheme 16) in initial experiments, it was found that n -benzylhydroxylamine o -benzoate 45 could be successfully employed as a monoalkylamine transfer agent for the hydroamination of styrene to afford the secondary amine in 60% yield and 96% ee. An in-depth computational mechanistic probe of the cuh-mediated hydroamination of internal arylalkynes with an archetype hydroxylamine ester and hydrosilane by a (xantphos)cuh catalyst (xantphos ≡ {p^p} ≡ 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene) is presented.

  • {p^p}cuh-mediated ha of styrene with amine electrophile 1b catalyst initiation effective ha catalysis entails the initial conversion of {p^p}cu(otbu) 2 into the catalytically competent {p^p}cu i hydride compound.

3 copper(i) hydride-catalyzed hydroamination – discovery, scope, and mechanistic insight in 2013, two research groups independently reported the cuh-catalyzed hydroamination of alkenes with n,n-dialkylhydroxylamine o-benzoates to produce tertiary amine products. An in-depth computational mechanistic probe of the cuh-mediated hydroamination of internal arylalkynes with an archetype hydroxylamine ester and hydrosilane by a (xantphos)cuh catalyst (xantphos.

cuh mediated hydroamination of styrene Excellent yields and enantioselectivities since then, cuh-catalyzed hydroamination has been extended to a wide scope of substrate classes, including vinyl silanes, terminal alkenes, internal unactivated alkenes, alkynes, and strained cyclic alkenes7,8 a general catalytic cycle for the hydroamination of styrene is shown in scheme 1. cuh mediated hydroamination of styrene Excellent yields and enantioselectivities since then, cuh-catalyzed hydroamination has been extended to a wide scope of substrate classes, including vinyl silanes, terminal alkenes, internal unactivated alkenes, alkynes, and strained cyclic alkenes7,8 a general catalytic cycle for the hydroamination of styrene is shown in scheme 1.
Cuh mediated hydroamination of styrene
Rated 3/5 based on 12 review
Download