- Palladium-tetraphosphine catalysed allylic substitution in water
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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.
- Feuerstein, Marie,Laurenti, Dorothée,Doucet, Henri,Santelli, Maurice
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- Practical regio- and stereoselective azidation and amination of terminal alkenes
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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.
- Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
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supporting information
p. 9354 - 9358
(2019/01/03)
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- Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides
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The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement pr
- West, Thomas H.,Spoehrle, Stéphanie S.M.,Smith, Andrew D.
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p. 4138 - 4149
(2017/06/29)
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- Palladium-tetraphosphine complex: An efficient catalyst for allylic substitution and Suzuki cross-coupling
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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.
- Feuerstein,Laurenti,Doucet,Santelli
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p. 2320 - 2326
(2007/10/03)
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- Dramatic acceleration of the catalytic process of the amination of allyl acetates in the presence of a tetraphosphine/palladium system
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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.
- Feuerstein,Laurenti,Doucet,Santelli
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- ?-Allyl palladium methodology for selective deprotection of allylamines. Practical synthesis of secondary amines
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The palladium-promoted deallylation of allylamines derived from primary and secondary amines is achieved with high to quantitative yield in the presence of 2-mercaptobenzoic acid as an allyl scavenger.This method was used for the sequential cleavage of diallylamines.A synthetic application of this procedure is presented in the preparation of secondary amines from diallylamines. - Keywords: allylamine; deallylation; sequential deprotection; ?-allyl palladium complexes; 2-mercaptobenzoic acid; substitution of amines
- Lemarie-Audoire, Sandrine,Savignac, Monique,Dupuis, Christophe,Genet, Jean Pierre
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p. 1157 - 1166
(2007/10/03)
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