Ortho-palladated imines as precursors of metallo-1,3-dipoles

Grigg, Ronald; Devlin, John L.

doi:10.1039/c39860000631

Cited by 25 publications

(10 citation statements)

References 2 publications

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“…Die Komplexe 1,2 und 11-18 setzen sich mit Do noren (PR 3, Pyridin, Aminosäureester) unter Spal tung der Chlorbrücken zu den einkernigen Ver bindungen 19 -35 um [10], wie auch von Grigg [5] beobachtet wurde. Diese Komplexe zeichnen sich durch wesentlich bessere Löslichkeit in organi schen Solventien aus.…”

Section: Ortho-palladierte Komplexeunclassified

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Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Böhm

Schreiner

Steiner

et al. 1998

Zeitschrift Für Naturforschung B

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The reactions o f Schiff bases from benzophenone and a-amino acid and peptide esters with tetrachloropalladate afford the chloro bridged ortho palladated complexes 1-8 and 11-18. The chloro bridges are cleaved by P and N donors (P R 3, pyridine, a-amino acid ester) to give the monomeric complexes 19 -35. From 1,2,3 and bidendate ligands (dppe, a-amino carboxylates, cysteine methyl ester) the bis(chelates) 36 -41, with N-diphenylmethylene glycylglycine ester the C,N ,N chelates 46 and 47 are obtained.The complexes 14, 23 and 47 were characterized by X-ray diffraction. Due to the two neighbouring five membered chelate rings in 47 a considerable distortion from the square planar coordination is observed.

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Section: Ortho-palladierte Komplexeunclassified

“…Grigg et al setz ten Schiff-Basen aus (substituiertem) Benzalde hyd und ct-Aminosäureester als Vorläufer für Metalla-l,3-dipole ein [5]. W ir berichteten über ei nen C,N,772-C=C-Palladium(II)-Komplex mit N-(Diphenylmethylen)-C-allylglycinester [6].…”

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Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Böhm

Schreiner

Steiner

et al. 1998

Zeitschrift Für Naturforschung B

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“…This reaction, however, gave the 1,4‐diene as the major product, which then had to be isomerized to the 1,3‐diene by using an iron complex. A more recently reported synthesis7 took advantage of another palladium‐catalyzed reaction: an intramolecular reductive vinyl bromide–alkyne coupling reaction developed by Grigg 10. This strategy, which required a number of functional‐group modifications, successfully provided the desired 1,3‐diene with the correct defined geometry.…”

Section: Methodsmentioning

confidence: 99%

Stereocontrolled Total Synthesis of (+)‐Streptazolin by a Palladium‐Catalyzed Reductive Diyne Cyclization

2004

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“…[610] By mentioning the extensive studies of metal catalyzed [3+2]-cycloadditions of azomethine ylides (prepared from Schiff bases of amino acid esters and aromatic carbonyl compounds) with activated olefins to give pyrrolidines (Equation (43)), [611][612][613][614][615] we are aware of going far beyond the scope of this review. Just for the record, none of the D1b-type metallo-azomethine ylides 146 has ever been isolated, however essential they are in this kind of processes.…”

Section: [3+2]-cycloaddition Reactions Of Metalla-13-dipolesmentioning

confidence: 99%

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Fehlhammer

Beck

2015

Zeitschrift anorg allge chemie

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Abstract. In whatever state of bonding -whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal -the azide moiety N 3 is characterized by its high potential of reactivity which essentially manifests itself in two basic processes: the elimination of dinitrogen and the entry into 1,3-dipolar cycloadditions with suitable dipolarophiles, the latter of which clearly predominates the chemistry of azide, also that of its metal compounds. In a preceding review entitled "Part I -Metal Azides: Overview, General Trends and Recent Developments" which was meant to lay the foundations for the present paper, these and other reactions have already been touched upon. The present review -Part II -now focusses in great detail on the formation of five-membered heterocyclestetrazol(at)es, triazol(at)es, triazolin(at)es, thiatriazol(at)es, etc. as well as various consecutive products -from azide and nitriles, isocyanides, alkynes, alkenes and heteroallenes (CS 2 , RN=C=S) in the ligand sphere of the metal. Generally, these [3+2]-cycloadditions are found to CONTENTS

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Ortho-palladated imines as precursors of metallo-1,3-dipoles

Cited by 25 publications

References 2 publications

Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Stereocontrolled Total Synthesis of (+)‐Streptazolin by a Palladium‐Catalyzed Reductive Diyne Cyclization

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Ortho-palladated imines as precursors of metallo-1,3-dipoles

Cited by 25 publications

References 2 publications

Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Metallkomplexe mit biologisch wichtigen Liganden, XCVIII Cyclopalladierte Schiff-Basen von α-Aminosäure- und Peptidestern/Metal Complexes of Biologically Important Ligands, XCVIII Cyclopalladated Schiff Bases of α-Amino Acid and Peptide Esters

Stereocontrolled Total Synthesis of (+)‐Streptazolin by a Palladium‐Catalyzed Reductive Diyne Cyclization

Azide Chemistry – An Inorganic Perspective, Part II[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems