Recent Advances in Catalytic Sequential Reactions Involving Hydroelement Addition to Carbon–Carbon Multiple Bonds

Zeng, Xiaoming

doi:10.1021/cr400082n

Cited by 442 publications

(144 citation statements)

References 456 publications

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“…2 Different from the conventional stepwise synthetic protocols, which suffer from complex reaction procedures, harsh reaction conditions, painful isolations, severe side reactions, etc., 3 sequential reactions enjoy unique atom economy, high efficiency, simple reaction and isolation procedures. 4 With these compelling advantages, sequential reactions have attracted much attention in promoting the elegance of synthesis and the development of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route

Deng

Lam

et al. 2015

Polym. Chem.

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Herein we reported a new facile one-pot multicomponent sequential polymerization approach for the construction of conjugated nitrogen-substituted polymers. Catalyzed by Pd(PPh3)2Cl2/CuI at room temperature, the couplinghydroamination polymerizations of 1,2-bis(4-ethynylphenyl)-1,2-diphenylethene, terephthaloyl chloride and secondary aliphatic amines proceeded smoothly in a regioregular and stereoselective manner, furnishing poly(arylene enaminone)s (PAEs) with high molecular weights (Mw up to 34 600) in satisfactory yields (up to 91%). Model compound was eleborately designed and synthesized to verify the chemical structures of the corresponding polymeric products. All the PAEs exhibited good solubility in common organic solvents and were thermally stable with degradation temperatures of up to 313 o C under nitrogen. They possessed good film-forming ability and their thin solid films showed high refractive indices (RI = 1.9318-1.6320) in a wide wavelength region of 400-1000 nm, whose value could be further modulated by UV irradiation. Although the model compound and the PAEs possessed a typical aggregation-induced emission luminogen of tetraphenylethene, they were weakly emissive either in solutioins or at the aggregated state, due to the photoinduced electron transfer (PET) effect. Their strong emission in the aggregated state could be readily recovered by blockage of the PET effect through protonation of the amino groups. Thus, this work demonstrated a powerful polymerization tool to access conjugated polymeric materials with pH-responsive properties.

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Section: Introductionmentioning

confidence: 99%

Regio- and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route

Deng

Lam

et al. 2015

Polym. Chem.

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“…Moreover, this new magnetic zeolite allows the simple separation of the catalyst with an external magnet [24] , which as already mentioned adds up to the added value of the active phase in terms of handling and reuse. This kind of reaction has become one of the most active research areas in pharmaceutical and fine chemical industries [25][26][27][28] .…”

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confidence: 99%

Magnetic zeolites: novel nanoreactors through radiofrequency heating

et al. 2017

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“…Numerous C-C bond formation reactions have been reported in the literature [28][29][30][31][32]. Carrying out multicomponent reactions (MCRs) for the coupling of two biologically active heterocyclic skeletons in aqueous media is an interesting subject in green chemistry [33][34][35][36][37][38][39][40]. In continuation of our research work to design one-pot reactions based on 3-formyl chromone 1a [41][42][43], herein we report an approach for the synthesis of new functionalized heterocycles, i.e., chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media and in the presence of a catalytic amount of K 2 CO 3 via a three-component reaction of 3-formylchromone 1, malononitrile or alkyl cyanoacetate 2, and cyclic 1,3-diones such as dimedone and barbiturates 3, and 4-hydroxy coumarin or 4-hydroxy-6-methyl-2-pyrone 5.…”

mentioning

confidence: 99%

Efficient synthesis of chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media

2015

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Recent Advances in Catalytic Sequential Reactions Involving Hydroelement Addition to Carbon–Carbon Multiple Bonds

Cited by 442 publications

References 456 publications

Regio- and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route

Regio- and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route

Magnetic zeolites: novel nanoreactors through radiofrequency heating

Efficient synthesis of chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media

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