54391-01-4Relevant articles and documents
PRODUCTION METHOD FOR 2-ALKENYLAMINE COMPOUND
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Paragraph 0045; 0047, (2014/07/22)
Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenyleamine compound is produced by 2-alkenylating a primary or secondary amine compound, using a specified 2-alkenylating agent and in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene.
Synthesis of pyrrole derivatives from diallylamines by one-pot tandem ring-closing metathesis and metal-catalyzed oxidative dehydrogenation
Chen, Weiqiang,Wang, Jianhui
supporting information, p. 1958 - 1963 (2013/05/08)
A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl 3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.
An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis
Sawadjoon, Supaporn,Samec, Joseph S. M.
scheme or table, p. 2548 - 2554 (2011/05/04)
The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.
Palladium nanoparticle-catalyzed C-N bond formation. A highly regio- and stereoselective allylic amination by allyl acetates
Adak, Laksmikanta,Chattopadhyay, Kalicharan,Ranu, Brindaban C.
scheme or table, p. 3982 - 3985 (2009/10/17)
(Chemical Equation Presented) Palladium nanoparticles, generated in situ from the reaction of palladium(II) chloride, have been demonstrated to be an efficient catalyst for C-N bond formation. A variety of aliphatic and aromatic amines have been allylated by substituted and unsubstituted allyl acetates in high yields by using palladium nanoparticles in the presence of a base without any ligand. The allylations are highly regio- and stereoselective.
Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol
Campbell, Matthew J.,Johnson, Jeffrey S.
, p. 1521 - 1524 (2008/02/02)
Equation Presented An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxyamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.
Pd·Et3B-catalyzed alkylation of amines with allylic alcohols
Kimura, Masanari,Futamata, Makoto,Shibata, Kazufumi,Tamaru, Yoshinao
, p. 234 - 235 (2007/10/03)
A combination of catalytic amounts of Pd (0.05 mmol) and Et3B (0.3 mmol) promotes allylic alkylation of primary and secondary aromatic and aliphatic amines (1.0 mmol) by the direct use of allylic alcohols, providing tertiary amines in excellent yields under mild conditions (room temperature ～ 50°C).
Indium-mediated barbier reactions of azides: A facile synthesis of N-allylamine derivatives
Yadav,Madhuri,Reddy,Reddy, G. S. Kiran Kumar,Sabitha
, p. 2771 - 2777 (2007/10/03)
N-Allylic amines are conveniently prepared in high yields by the reaction of azides with allylindium reagents in the presence of sodium iodide in DMF at ambient temperature.
Palladium-tetraphosphine complex: An efficient catalyst for allylic substitution and Suzuki cross-coupling
Feuerstein,Laurenti,Doucet,Santelli
, p. 2320 - 2326 (2007/10/03)
A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane (Tedicyp) has been synthesized and used in palladium-catalyzed reactions. This tetraphosphine in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for coupling reactions. Turnover numbers of 980 000 for allylic amination, 9 800 000 for allylic alkylation and 97 000 000 for Suzuki cross-coupling can be obtained in the presence of this catalyst.
Palladium-tetraphosphine catalysed allylic substitution in water
Feuerstein, Marie,Laurenti, Dorothée,Doucet, Henri,Santelli, Maurice
, p. 2313 - 2315 (2007/10/03)
The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl (C3H5)]2 system catalyses allylic amination in water with very high substrate/catalyst ratio in good yields. A turnover number of 980 000 can be obtained for the addition of dipropylamine to allyl acetate in the presence of this catalyst.
Dramatic acceleration of the catalytic process of the amination of allyl acetates in the presence of a tetraphosphine/palladium system
Feuerstein,Laurenti,Doucet,Santelli
, p. 43 - 44 (2007/10/03)
The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 system catalyses allylic amination in good yields with a very high substrate/catalyst ratio; a turnover number of 680 000 and a turnover frequency of 8125 h-1 can be obtained for the addition of dipropylamine to allyl acetate in the presence of this catalyst.
