In situ cuprate formation via transmetalation between vinylstannanes and higher order cyanocuprates

Behling, James R.; Babiak, Kevin A.; Ng, John S.; Campbell, Arthur L.; Moretti, Robert; Koerner, M.; Lipshutz, Bruce H.

doi:10.1021/ja00216a045

Cited by 162 publications

(45 citation statements)

References 2 publications

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“…[88] Moreover, the role of the copper as aryl carrier in the transmetalation mechanism was consistent with the previous observation that vinyl cuprates are efficiently formed by reacting vinylstannanes with organocuprates. [89] In common solvents and milder conditions, Liebeskind proposed that CuI simply scavenges L from [PdArXL 2 ] complexes in the case of strong donor ligands (L = PPh 3 ); for weak donor ligands (L = AsPh 3 ) the effect is negligible because spontaneous AsPh 3 dissociation from [PdArXL 2 ] is quite efficient. [88] Espinet and co-workers carried out a quantitative evaluation of this second kind of "copper effect", with copper acting as ligand scavenger in THF, and discovered that in fact CuI does not scavenge PPh 3 from [PdArIA C H T U N G T R E N N U N G (PPh 3 ) 2 ].…”

Section: A C H T U N G T R E N N U N G (Pph 3 ) 2 ]/A C H T U N G T Rmentioning

confidence: 99%

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Pérez‐Temprano

Casares

Espinet

2012

Chemistry A European J

217

131

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Bimetallic catalysis refers to homogeneous processes in which either two transition metals (TM), or one TM and one Group 11 (G11) element (occasionally Hg also), cooperate in a synthetic process (often a C-C coupling) and their actions are connected by a transmetalation step. This is an emerging research area that differs from the isolated or tandem applications of the now classic processes (Stille, Negishi, Suzuki, Hiyama, Heck). Most of the reactions used so far combine Pd with a second metal, often Cu or Au, but syntheses involving very different TM couples (e.g., Cr/Ni in the catalyzed vinylation of aldehydes) have also been developed. Further development of the topic will soon demand a good knowledge of the mechanisms involved in bimetallic catalysis, but this knowledge is very limited for catalytic processes. However, there is much information available, dispersed in the literature, coming from basic research on exchange reactions occurring out of any catalytic cycle, in polynuclear complexes. These are essentially the same processes expected to operate in the heart of the catalytic process. This Review gathers together these two usually isolated topics in order to stimulate synergy between the bimetallic research coming from more basic organometallic studies and the more synthetic organic approaches to this chemistry.

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Section: A C H T U N G T R E N N U N G (Pph 3 ) 2 ]/A C H T U N G T Rmentioning

confidence: 99%

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Pérez‐Temprano

Casares

Espinet

2012

Chemistry A European J

217

131

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“…However, the diastereoselectivity issue at the C-4 position needed to be addressed by experiment. To synthesize 15, we used Lipshultz's procedure [19] to generate the corresponding high order cuprate because transmetallation of tetraisopropenyltin to the corresponding cuprate with MeLi was not successful. Thus, lithium diisopropenylcyanocuprate was prepared by reacting tetraisopropenyltin with freshly prepared Me 2 CuCNLi 2 .…”

Section: -Methyl-3-pipecolinoglutamic Acid (3)mentioning

confidence: 99%

Application of rhodium-catalyzed cyclohydrocarbonylation to the syntheses of enantiopure homokainoids

Chiou¹,

Schoenfelder

Mann

et al. 2008

Pure and Applied Chemistry

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Kainic acid, rigidified (S)-glutamic acid, is a well-known kainite receptor agonist for the excitatory transmission in the central nerve system. Our interest in highly selective kainite ligands, prompted us to design a series of new kainic homologues, "homokainoids", i.e., conformationally rigidified (S)-glutamic acids. For the syntheses of enantiopure novel homokainoids (pipecolinoglutamic acids), we successfully applied cyclohydrocarbonylation (CHC) reaction that has been developed in these laboratories. Efficient total syntheses of enantiopure novel homokainoids from (R)-serine feature the highly diastereoselective conjugate addition and the regioselective CHC process in the key steps.

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“…A total stereoselective route for this prostaglandin has not yet been reported. Described herein is a simple and efficient synthesis of 1 via a two component coupling process (Scheme 1) [8] .…”

Section: Introductionmentioning

confidence: 99%

Effective Stereoselective Total Synthesis of 16,16-Dimethyl Prostaglandin E2

Rodrı́guez¹,

Nomen²,

Spur³

et al. 1998

Arch. Pharm. Pharm. Med. Chem.

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In situ cuprate formation via transmetalation between vinylstannanes and higher order cyanocuprates

Cited by 162 publications

References 2 publications

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Bimetallic Catalysis using Transition and Group 11 Metals: An Emerging Tool for CC Coupling and Other Reactions

Application of rhodium-catalyzed cyclohydrocarbonylation to the syntheses of enantiopure homokainoids

Effective Stereoselective Total Synthesis of 16,16-Dimethyl Prostaglandin E2

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