2004
DOI: 10.1002/anie.200300634
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Nickel‐Catalyzed Reductive Cyclizations and Couplings

Abstract: For over 50 years, nickel catalysis has been applied in cycloaddition processes. Nickel-catalyzed reductive couplings and cyclizations, however, have only recently attracted a high level of interest. This group of new reactions allows a broad range of multicomponent couplings involving two or more pi components with a main-group or transition-metal reagent. These processes allow the assembly of important organic substructures from widely available reaction components. Multiple contiguous stereocenters, polycyc… Show more

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Cited by 654 publications
(184 citation statements)
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“…[2][3][4] Although more functionalized conjugate carbonyls and dienes are used as one of the partners, [5,6] the direct addition of monoenes to these systems is also an important advance in the field. [7,8] Recently, some of these alkene coupling technologies have been developed to achieve the asymmetric synthesis of biologically important molecules, with ibuprofen being a representative example. [6e, 9] Nevertheless, all of the above methods are either characterized by head-to-head (h-h) or tail-to-head (t-h) C-C bond formation or use ethylene as one of the components; tail-totail (t-t) hetero-hydroalkenylation should provide branched terminal 1,1-disubstituted alkenes, but such products are observed only in small amounts, or in intramolecular cases wherein the geometric constraints of ring closure play a substantial role.…”
mentioning
confidence: 99%
“…[2][3][4] Although more functionalized conjugate carbonyls and dienes are used as one of the partners, [5,6] the direct addition of monoenes to these systems is also an important advance in the field. [7,8] Recently, some of these alkene coupling technologies have been developed to achieve the asymmetric synthesis of biologically important molecules, with ibuprofen being a representative example. [6e, 9] Nevertheless, all of the above methods are either characterized by head-to-head (h-h) or tail-to-head (t-h) C-C bond formation or use ethylene as one of the components; tail-totail (t-t) hetero-hydroalkenylation should provide branched terminal 1,1-disubstituted alkenes, but such products are observed only in small amounts, or in intramolecular cases wherein the geometric constraints of ring closure play a substantial role.…”
mentioning
confidence: 99%
“…Nickel-catalyzed cyclizations, couplings, and cycloadditions involving three reactive components have been an active area of research for the past decade [39,40]. Central to these reactions is the involvement of a low-valent nickel capable of facilitating oxidative coupling of an unsaturated hydrocarbon (such as an alkyne, allene, or alkene) and a carbonyl substrate (such as an aldehyde or ketone).…”
Section: Reductive Coupling Reactions In the Presence Of A Reductantmentioning
confidence: 99%
“…[11,12] Over the past decade, nickel-catalyzed reductive cyclizations and couplings have evolved into a broadly useful strategy for assembling synthetically versatile substructures and complex molecules. [13] Moreover, chiral nickel complexes are becoming potential practical catalysts in enantioselective transformations. [14] Also, as excellent chiral scaffolds, N,N'-dioxidemetal complexes have exhibited great potential in many asymmetric reactions.…”
Section: Introductionmentioning
confidence: 99%