Structural Differences between Open-Chain and Macrocyclic Triene Ligands for Palladium(0): Influence on the Stability and Catalytical Properties

Dachs, Anna; Masllorens, Judit; Pla‐Quintana, Anna; Roglans, Anna; Farjas, Jordi; Parella, Teodor

doi:10.1021/om800544h

Cited by 6 publications

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“…In recent years, following the unexpected discovery of an ( E,E,E )-1,6,11-triazacyclopentadeca-3,8,13-triene–Pd(0) complex, the Roglans group has worked intensively on the synthesis of a series of azamacrocycles with various ring sizes and numbers of CC and CC bonds . The ability of these macrocycles to coordinate at Pd(0), Pt(0), and Ag(I) has been studied, with particular success in the stabilization of palladium(0) (structures II , III , and IV in Figure ).…”

Section: Introductionmentioning

confidence: 99%

Nickel(0) Complexes of Polyunsaturated Azamacrocyclic Ligands

et al. 2012

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A series of nickel(0) complexes, 3, 4, and 5, containing unsaturated 15-membered azamacrocyclic ligands have been synthesized. Structural characterization of the complexes is based on NMR spectroscopy, X-ray diffraction analysis, and differential scanning calorimetry. In addition, the catalytic activity of the complexes in the Suzuki–Miyaura cross-coupling of arylboronic acids and aryl halides has been tested.

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Section: Introductionmentioning

confidence: 99%

Nickel(0) Complexes of Polyunsaturated Azamacrocyclic Ligands

et al. 2012

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“…The Roglans group, following the unexpected discovery of a Pd(0)–( E , E , E )-1,6,11-triazacyclopentadeca-3,8,13-triene complex, has worked intensively on the synthesis of a series of azamacrocycles with various ring sizes and numbers of CC and CC bonds . These macrocycles have been coordinated to Pd(0), Pt(0), and Ag(I) to afford complexes such as IV – VI , which contain a 15-membered ring ligand with the ene/yne groups in 1,6,11-sequences.…”

Section: Introductionmentioning

confidence: 99%

Nickel(0) Complexes of Acyclic Polyunsaturated Aza Ligands

et al. 2013

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The acyclic 4,9-bis(4-tolylsulfonyl)-4,9-diazadodeca-1,11dien-6-yne (1) and 4,9-bis(4-tolylsulfonyl)-4,9-diazatrideca-1,(E)-6-dien-11-yne (2), which differ in the sequence of the two ene and one yne functions in the chain, have been reacted with 1 and 2 equiv of Ni(cod) 2 . The reaction with 1 equiv of Ni(cod) 2 affords the mononuclear trigonalplanar nickel(0) complexes 3 and 5. These react with a further 1 equiv of Ni(cod) 2 by addition of a Ni(cod) entity to give the dinuclear derivatives 4 and 6. While 3 forms a mixture of isomers C 2 -3 and C s -3 in solution, C 2 -3 is exclusively present in the crystal, where it is packed in parallel columns. Complex 6 crystallizes as a spherulite. Complexes 3−6 have been characterized by NMR and single-crystal X-ray structure analysis, and a detailed conformational analysis is given.

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Cross‐Coupling Reactions of Organotrifluoroborate Salts

Molander

Jean‐Gérard

2012

Organic Reactions

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Organotrifluoroborates are partners for cross‐coupling that have emerged as complementary and often unique alternatives to other organoboron reagents. This chapter provides a comprehensive overview of all cross‐coupling reactions of the various classes of organotrifluoroborates that have been carried out through August, 2009. The chapter introduces the subject with a discussion of mechanistic considerations concerning the cross‐coupling, followed by a brief discussion of the stereochemical aspects of the transformation. The scope and limitations of the reactions are subsequently discussed, first in terms of the organotrifluoroborate and then the electrophilic partner of the reaction. Potential side reactions that are encountered are outlined with useful suggestions on how these can be avoided in practice. Applications in synthesis are described, detailing how organotrifluoroborates have been utilized in the construction of natural products, materials of all types, and pharmacologically active substances. A comparison to other cross‐coupling methods rounds out the descriptive part of the chapter. A detailed outline of experimental considerations and protocols has been assembled, gleaning information from the vast array of published procedures to assemble an overview of the most successful conditions. Representative procedures are included for each class of organotrifluoroborate coupling partner, and the tables provide a comprehensive listing of individual reactions.

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Structural Differences between Open-Chain and Macrocyclic Triene Ligands for Palladium(0): Influence on the Stability and Catalytical Properties

Cited by 6 publications

References 44 publications

Nickel(0) Complexes of Polyunsaturated Azamacrocyclic Ligands

Nickel(0) Complexes of Polyunsaturated Azamacrocyclic Ligands

Nickel(0) Complexes of Acyclic Polyunsaturated Aza Ligands

Cross‐Coupling Reactions of Organotrifluoroborate Salts

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