Reaction of amines with 1,3-dienes catalysed by nickel complexes

Baker, Raymond; Cook, A. H.; Halliday, D. E.; Smith, Trevor N.

doi:10.1039/p29740001511

Cited by 31 publications

(11 citation statements)

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“…The suppression of trans,trans,cis-cdt formation on addition of pyridine is in keeping with this suggestion since it is known that pyridine facilitates the r} 3 -+-T; 1 -allyl interconversion. (35) PMe 3 PMe,…”

Section: Methodsmentioning

confidence: 99%

“…The catalysts mentioned above cyclodimerize butadiene to a mixture of 1,5-cyclooctadiene (cod), 4-vinylcyclohexene (vch) and d.?-l,2-divinylcyclobutane (dvcb), (l)- (3). The yield of cyclodimer is highest with a nickel: ligand ratio of 1:1; lower ligand concentrations favour cyclotrimerization, and higher concentrations lead to interconversion between cod and vch.…”

Section: The Cyclodimerization Of Butadienementioning

confidence: 99%

“…89 Octadienylated methylhydrazones have also been shown to be formed in a stoichiometric reaction between [NiPPh 3 (77 3 ,77 3 intermediates involved are possible and it has, moreover, been suggested that the /3-hydrogen transfer step occurs as a sigmatropic rearrangement within the complex without involving the nickel atom. 72 Complexes related to the intermediates shown in the Scheme have been isolated from the stoichiometric reaction between [Ni(cod)2], 1,3-dienes and Schiff bases.…”

mentioning

confidence: 99%

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Nickel Catalyzed Oligomerization of 1,3-Dienes and Related Reactions

Jolly¹

1982

Comprehensive Organometallic Chemistry

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Section: Methodsmentioning

confidence: 99%

Section: The Cyclodimerization Of Butadienementioning

confidence: 99%

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confidence: 99%

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Nickel Catalyzed Oligomerization of 1,3-Dienes and Related Reactions

Jolly¹

1982

Comprehensive Organometallic Chemistry

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“…However, by passing 1,3-butadiene gas into a solution of NiBr 2 /PhP(Oi-Pr) 2 in morpholine, 1-(N-morpholino)-2-butene could be obtained highly selectively (Eq. 4.45) [179]. In the early stages of the reaction, a mixture of 3-(N-morpholino)-1-butene and 1-(N-morpholino)-2-butene is formed, which fully isomerizes into 1-(N-morpholino)-2-butene [179].…”

Section: Activation Of the Dienementioning

confidence: 99%

“…4.45) [179]. In the early stages of the reaction, a mixture of 3-(N-morpholino)-1-butene and 1-(N-morpholino)-2-butene is formed, which fully isomerizes into 1-(N-morpholino)-2-butene [179].…”

Section: Activation Of the Dienementioning

confidence: 99%

Catalytic Hydroamination of Unsaturated Carbon‐Carbon Bonds

Brunet

Neibecker

2001

Catalytic Heterofunctionalization

139

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Hydroamination of Alkenes

Reznichenko

Hultzsch

2015

Organic Reactions

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The addition of an amine NH‐functionality to alkenes (including vinyl arenes, conjugated dienes, allenes or ring‐strained alkenes), the so‐called hydroamination, represents a simple and highly atom‐economical approach for the synthesis of nitrogen‐containing products. A large variety of catalyst systems are available, ranging from alkali, alkaline earth, rare earth, Group 4 and Group 5 metals, to late transition metal catalysts, and, less prominent, Brønsted and Lewis acid‐based catalyst systems. The mode of operation of these catalyst systems can vary significantly and the different reaction mechanisms and the scope and limitations are discussed. While intramolecular hydroamination reactions can be readily achieved with a large number of catalyst systems, significantly fewer examples for the more challenging intermolecular hydroamination are known, especially for unactivated alkenes. The stereoselective hydroamination has also received significant attention due to the importance of chiral nitrogen‐containing molecules in pharmaceutical industry. A variety of highly selective chiral catalyst systems have been developed for intramolecular hydroaminations, while examples of intermolecular asymmetric hydroaminations are scarce. Hydroamination in the context of this review article is defined as the addition of HNR 2 across a non‐activated, unsaturated carbon‐carbon multiple bond. This review focuses on the hydroamination reaction of simple, non‐activated alkenes. The addition of amines to slightly activated alkenes, such as vinyl arenes, 1,3‐dienes, strained alkenes (norbornene derivatives, methylenecyclopropenes) and allenes is closely related and is covered as well. However, hydroamination reactions of alkynes and Aza‐Michael reactions involving the addition of an N‐H fragment across the conjugated or otherwise activated double bond of a Michael acceptor are not covered. The scope of amine types includes ammonia, primary and secondary aliphatic and aromatic amines, azoles, and hydrazines. N ‐Protected amines, such as ureas, carboxamides, and sulfonamides are covered as well, as they are important substrates for metal‐free and late transition metal‐based catalysts. The literature through January 2011 will be covered with two selected references from 2012 (comprising Table 3D). A supplemental reference list is provided for reports appearing February 2011 through April 2015. The chapter is organized by the nature of the carbon unsaturation to which the amine is added. Ranging from less reactive substrates such as ethylene and unactivated alkenes, to slightly activated substrates, such as vinyl arenes, and more activated substrates, including conjugated dienes, allenes and strained alkenes. Enantioselective hydroamination reactions, an area that has seen significant progress over the past decade, are discussed next. Finally, tandem hydroamination/carbocyclization reactions of aminodialkenes provide rapid access to complex alkaloidal skeletons. The tables at the end of the chapter are separated into five main sections: achiral intermolecular hydroamination, achiral intramolecular hydroamination, enantioselective intermolecular hydroamination, enantioselective intramolecular hydroamination, and tandem hydroamination/carbocyclization. Within the first four sections the tables are further divided into subsections based on the participating alkene, i.e. alkenes, vinyl arenes, dienes, allenes, and strained alkenes.

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Reaction of amines with 1,3-dienes catalysed by nickel complexes

Cited by 31 publications

References 0 publications

Nickel Catalyzed Oligomerization of 1,3-Dienes and Related Reactions

Nickel Catalyzed Oligomerization of 1,3-Dienes and Related Reactions

Catalytic Hydroamination of Unsaturated Carbon‐Carbon Bonds

Hydroamination of Alkenes

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