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• 98088-48-3 1-(allyloxy)-1-phenylbut-3-ene 
• 145610-58-8 N-allyl-N-tosyl-α,α,α-trichloroacetamide 

Relevant academic research and scientific papers

Intramolecular metathesis versus Kharasch reactions using the Grubbs metathesis catalyst: Towards catalyst economy

The first generation Grubbs catalyst can promote either ring closing metathesis (RCM) or atom transfer radical cyclisation reactions (ATRC) depending upon the reaction conditions employed.

Ligand electronic effects on rates of copper mediated atom transfer radical cyclisation and polymerisation

The effect of different N-pentyl-2-pyridylmethanimine derivatives 2a-f upon the rate of copper(I) mediated atom transfer radical cyclisation (ATRC) of 5 and living atom transfer radical polymerisation (ATRP) of methylmethacrylate were investigated.

Atom-transfer radical reactions catalyzed by a coordinatively unsaturated diruthenium amidinate, [(η5-C5Me5) Ru(μ2-i-PrNC(Me)Ni-Pr)Ru(η5-C5Me 5)]+

Atom-transfer radical cyclization (ATRC) and addition (ATRA) catalyzed by a coordinatively unsaturated diruthenium amidinate complex 4, [(η5-C5Me5)Ru(μ2-i-PrNC(Me) Ni-Pr)Ru(η5-C5Me5/s

Atom Transfer Radical Cyclisations Mediated by the Grubbs Ruthenium Metathesis Catalyst

The commercially available ruthenium carbene complex RuCl 2(=CHPh)(PCy3)2 efficiently catalyses the cychsation of halo alkenes to γ-lactones and γ-lactams.

Catalytic atom-transfer radical cyclization by copper/bipyridine species encapsulated in polysiloxane gel

Novel polysiloxane gel, in which CuCl/bipyridine species are immobilized, is prepared by treatment of polymethylhydrosiloxane with 4,4′-bis[(2- propenyl)oxy]-2,2′-bipyridine and 1,5-hexadine in the presence of Karstedt′s catalyst followed by addition of CuCl. This polysiloxane gel acts as a reusable catalyst in the atom-transfer radical cyclization of α-halogenated acetamide derivatives in high turnover numbers without allowing leakage of the metal species.

New reactivity patterns of copper(I) and other transition metal NHC complexes: application to ATRC and related reactions

Pre-formed transition metal-NHC complex is shown to be an effective catalyst for Atom Transfer Radical Cyclisation (ATRC) reactions.

Solid-supported copper catalysts for atom-transfer radical cyclizations: Assessment of support type and ligand structure on catalyst performance in the synthesis of nitrogen heterocycles

A range of solid supported pyridinemethanimine 9-11 and polyamine 12-15 ligands have been prepared on silica, polystyrene, and JandaJel supports. The CuCl and CuBr complexes of these supported ligands have been used to assess both the effect of the ligand type and the nature of the support upon a representative range of copper-mediated atom transfer 5-exo-trig 6, 24-25, 5-exo-dig 26, 4-exo-trig 28, and 5-endo-trig 27, 38 radical cyclizations to give nitrogen heterocycles. In addition, the effect of the nature of the support on the stereochemical outcome of the 5-exo cyclization of 25 has been probed. Generally, it was found that the type of support (e.g., polystyrene, silica, or JandaJel) had very little effect upon the efficiency and selectivity of the processes but that the nature of the ligand type immobilized was the important factor. Thus, the 5-exo cyclization of 6 and 24-26 proceeded more rapidly with the PMI ligands 9-11, whereas 4-exo cyclizations 28 and 5-endo radical polar crossover reactions 27 and 38 proceeded more efficiently with the JJ-TEDETA ligand 15. The efficiency of the supported ligands was also compared to their solution counterparts 4 and 5. The reusability of P-PMDETA ligand system 13 was assessed in the cyclization of 6.

A cationic diruthenium amidinate, [(η5-C5Me 5)Ru(μ2-i-PrN=C(Me)Ni-Pr)Ru(η5-C 5Me5)]+, as an efficient catalyst for the atom-transfer radical reactions

A cationic diruthenium amidinate, [(η5-C5Me 5)Ru(μ2-i-PrN=C(Me)Ni-Pr)Ru(η5-C 5Me5)]+, is generated by treatment of (η5-C5Me5)Ru(μ

Organoruthenium(II) and (III) amidinates, (η5-C5Me5)Ru(η-amidinate) and (η5-C5Me5)RuCl(η-amidinate), as unique redox catalysts for the intramolecular Kharasch reactions: Facile access to a pyrrolizidine alkaloid skeleton under mild c

A novel organoruthenium amidinate, (η5-C5Me5)RuCl(η-(i-Pr)N=C(Me)N(i-Pr)) (2), has been prepared by oxidation of organoruthenium amidinate, (η5-C5Me5)Ru(η-(iPr)N=C-Me)N(i-Pr)) (1), by organic chlorides; both 1 and 2 are found to be g

Atom transfer radical cyclisations of activated and unactivated N-allylhaloacetamides and N-homoallylhaloacetamides using chiral and non-chiral copper complexes

Activated N-tosyl-2,2,2-trichloroacetamide 6a, N-benzyl-2,2,2-trichloroacetamide 6d, 2,2-dichloroacetamides 6b-c and 6e-f and 2-monohaloacetamides lla-g undergo efficient 5-exo atom transfer radical cyclisations at room temperature mediated by CuCl or CuBr in the presence of tris(N,N-dimethylaminoethylene)amine 3 (trien-Me6). The efficiency and stereoselectivity of these cyclisations was found to be greater than existing published atom transfer procedures based upon CuCl(bipyridine), RuCl2(PPh3)3 and CuCl(TMEDA)2. The product distribution for the cyclisation onto alkyne 11g was found to be solvent dependent. Attempts to make larger ring sizes by endo cyclisation of N-tosylacetamides 19a-c led to a competing 5-exo ipso aromatic substitution into the N-tosyl group followed by re-aromatisation and loss of SO2 to furnish an amidyl radical. Cyclisation of N-homoallylacetamides 25a-d proceeded smoothly to give δ-lactams with a range of catalysts based upon ligands 2 and 26. The stereoselectivity of cyclisation to give γ lactams could be somewhat influenced by using chiral enantiopure copper complexes 28-30 suggesting that the reactions may involve metal-complexed radicals.