Relevant bibliographies by topics / Migratory-insertion reactions

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  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Migratory-insertion reactions'

Author: Grafiati
Published: 4 June 2021
Last updated: 17 February 2022

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Journal articles on the topic "Migratory-insertion reactions"

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Adeyemi, Olalere G., and Neil J. Coville. "Solvent-Free Organometallic Migratory Insertion Reactions." Organometallics 22, no. 11 (May 2003): 2284–90. http://dx.doi.org/10.1021/om0301738.

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Xia, Ying, Yan Zhang, and Jianbo Wang. "Catalytic Cascade Reactions Involving Metal Carbene Migratory Insertion." ACS Catalysis 3, no. 11 (October 22, 2013): 2586–98. http://dx.doi.org/10.1021/cs4006666.

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Zeidan, Nicolas, and Mark Lautens. "Migratory Insertion Strategies for Dearomatization." Synthesis 51, no. 22 (August 26, 2019): 4137–46. http://dx.doi.org/10.1055/s-0037-1611918.

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Development of strategies for molecule functionalization by dearomatization has surged in the last two decades. The benefits of overcoming the resonance stabilization energy outweigh the cost; diverse compounds could be accessed in a short number of steps. One approach that has been of interest in recent years is the dearomatization of indoles and other (hetero)aromatic compounds by migratory insertion. The chiral σ-bond palladium intermediate could be reduced or trapped by a second functionalization. In this short review we will summarize the recently discovered reactions from our group and others in this field of metal-catalyzed dearomatizations by migratory insertion.1 Introduction2 Monofunctionalizations: Heck and Reductive Heck Reactions2.1 N-Tethered Heterocycles2.2 Non-N-tethered Heterocycles2.3 Non-heterocycles3 Dearomative Difunctionalizations: Interrupted Heck Reaction3.1 N-Tethered Heterocycles3.2 Non-N-tethered Heterocycles4 Conclusion
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Walewska, Małgorzata, Judith Baumgartner, and Christoph Marschner. "1,2- and 1,1-Migratory Insertion Reactions of Silylated Germylene Adducts." Molecules 25, no. 3 (February 6, 2020): 686. http://dx.doi.org/10.3390/molecules25030686.

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The reactions of the PMe3 adduct of the silylated germylene [(Me3Si)3Si]2Ge: with GeCl2·dioxane were found to yield 1,1-migratory insertion products of GeCl2 into one or two Ge–Si bonds. In a related reaction, a germylene was inserted with tris(trimethylsilyl)silyl and vinyl substituents into a Ge–Cl bond of GeCl2. This was followed by intramolecular trimethylsilyl chloride elimination to another cyclic germylene PMe3 adduct. The reaction of the GeCl2 mono-insertion product (Me3Si)3SiGe:GeCl2Si(SiMe3)3 with Me3SiC≡CH gave a mixture of alkyne mono- and diinsertion products. While the reaction of a divinylgermylene with GeCl2·dioxane only results in the exchange of the dioxane of GeCl2 against the divinylgermylene as base, the reaction of [(Me3Si)3Si]2Ge: with one GeCl2·dioxane and three phenylacetylenes gives a trivinylated germane with a chlorogermylene attached to one of the vinyl units.
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DeLuca, Ryan J., Benjamin J. Stokes, and Matthew S. Sigman. "The strategic generation and interception of palladium-hydrides for use in alkene functionalization reactions." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 395–408. http://dx.doi.org/10.1515/pac-2014-5041.

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Abstract We review methods that our lab has developed for the generation of Pd-hydrides and the manipulation of these useful intermediates via β-hydride elimination and migratory insertion steps. For a given alkene functionalization reaction, careful understanding of the dynamics of β-hydride elimination, migratory insertion, and transmetallation have allowed for the selective functionalization of Pd-alkyl intermediates. This has afforded us a means by which to transpose palladium to a desired position on a substrate for subsequent functionalization, empowering a number of useful C–H, C–O, and C–C bond-forming reactions.
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Fernández-Galán, Rafael, Antonio Antiñolo, Fernando Carrillo-Hermosilla, Isabel López-Solera, Antonio Otero, Amparo Serrano-Laguna, and Elena Villaseñor. "Migratory Insertion Reactions in Asymmetrical Guanidinate-Supported Zirconium Complexes." Organometallics 31, no. 23 (November 29, 2012): 8360–69. http://dx.doi.org/10.1021/om300942p.

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Xia, Ying, Yan Zhang, and Jianbo Wang. "ChemInform Abstract: Catalytic Cascade Reactions Involving Metal Carbene Migratory Insertion." ChemInform 45, no. 2 (December 19, 2013): no. http://dx.doi.org/10.1002/chin.201402237.

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Mazzacano, Thomas J., Noel J. Leon, Greyson W. Waldhart, and Neal P. Mankad. "Fundamental organometallic chemistry under bimetallic influence: driving β-hydride elimination and diverting migratory insertion at Cu and Ni." Dalton Transactions 46, no. 17 (2017): 5518–21. http://dx.doi.org/10.1039/c6dt04533b.

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BI, SIWEI, JUNFENG ZHAO, WEI FAN, and PING LI. "A DFT STUDY OF CO MIGRATORY INSERTION REACTIONS WITH A NEW TYPE OF GROUP 10 METAL-ALKYL AND METAL-ALKOXIDE BONDS." Journal of Theoretical and Computational Chemistry 11, no. 01 (February 2012): 1–17. http://dx.doi.org/10.1142/s0219633612500010.

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The CO migratory insertion into M–O and M–C bonds of the new model (PMe3)2M(η2 – CH2CH2O) ( M = Ni , Pd and Pt ) (model (d)) proposed in this work has been studied with the aid of density functional theory (DFT) calculations. It is found (1) when M = Ni , CO migratory insertion into Ni–C is thermodynamically and kinetically favored, and (2) when M = Pd and Pt , the insertion into M–O bond via a one-step process is preferred. Further investigation on CO migratory insertion using Pt(PMe3)2(C7H10O) (R′-Pt) derived from the experimental compound Pt(PEt3)2(C7H10O) gives the same conclusions as model (d) with M = Pt . Results obtained from the reaction of model (d) ( M = Pt ) with CO are consistent with the experimental observation that CO prefers to insert into Pt–O bond of Pt(PEt3)2(C7H10O) .
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Paraja, Miguel, and Carlos Valdés. "Pd-catalyzed cascade reactions between o-iodo-N-alkenylanilines and tosylhydrazones: novel approaches to the synthesis of polysubstituted indoles and 1,4-dihydroquinolines." Chemical Communications 52, no. 37 (2016): 6312–15. http://dx.doi.org/10.1039/c6cc01880g.

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Dissertations / Theses on the topic "Migratory-insertion reactions"

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Serra, Parareda Jordi. "Gold complexes for homogeneous cross-coupling catalysis and migratory insertion reactions." Doctoral thesis, Universitat de Girona, 2018. http://hdl.handle.net/10803/664428.

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Most of the different homogeneous reactions catalyzed by gold have been developed in the past fifteen years and stem from the ability of both Au(I) and Au(III) complexes to coordinate and activate multiple carbon-carbon bonds. However, the high ionization potential of gold has long hindered Au(I)/Au(III) catalytic cycles under homogeneous conditions, an underdeveloped field compared to classical cross-coupling methodologies. Although direct evidence for the main elementary steps of organometallic chemistry has been obtained very recently, their scope is still limited and much remains to be done before our knowledge on gold reaches that of other transition metals, especially of groups 9 and 10. Therefore, the unifying motivation behind the different research topics presented in this doctoral dissertation is to enhance our expertise concerning the factors governing the reactivity of gold complexes, with oxidative addition and migratory insertion particularly under the spotlight
La majoria de reaccions homogènies catalitzades per or han estat desenvolupades els darrers quinze anys, i aprofiten la capacitat dels complexes d’Au(I) i Au(III) per coordinar i activar enllaços múltiples carboni-carboni. No obstant l'elevat potencial de ionització de l’or ha privat l’accés a cicles catalítics del tipus Au(I)/Au(III) en condicions homogènies, un camp subdesenvolupat en comparació amb d’altres metodologies d’acoblament creuat clàssiques. Malgrat que recentment els processos fonamentals en química organometàl·lica han estat evidenciats, el seu abast és encara limitat i queda molt per recórrer abans que el nostre coneixement en or assoleixi el d’altres metalls de transició. Així doncs, la motivació principal rere els projectes de recerca presentats en aquesta tesi doctoral és incrementar la nostra expertesa pel que fa als factors que governen les reactivitat dels complexes d’or, amb especial incidència en l’addició oxidant i la inserció migratòria
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Evans, Anthony Steven. "Mechanism of the Heck reaction: nature of oxidative addition and migratory insertion." Thesis, Texas A&M University, 2004. http://hdl.handle.net/1969.1/1130.

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The mechanism of carbon coupling reactions is traditionally represented in a very broad schematic. This thesis seeks to explore the mechanism of these reactions by focusing on Heck olefination. The Heck reaction has become a powerful tool in synthetic labs but the mechanism of this reaction has remained a topic of debate since the reaction's discovery. The catalytic cycle that has come to be accepted, while accurate in its own right, is not nearly as detailed as the complexity of the various stages of the Heck reaction suggest it should be. This study seeks to elucidate the nature of the oxidative addition of aryl halide to a palladium catalyst using a ligand that has been shown to have high activity in facilitating oxidative addition of aryl chlorides and bromides in other coupling reactions. This information is then compared to other studies in the field so that conclusions can be drawn about the oxidative addition. Also, selectivity studies seek to determine the nature of the migratory insertion of an olefin into the Pd-Ar bond. Again, comparison of results obtained in this study are compared to previous results so that a more definitive conclusion can be drawn about the oxidative addition.
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Evans, Anthony Steven. "Mechanism of the Heck reaction: nature of oxidative addition and alkene insertion." Thesis, Texas A&M University, 2004. http://hdl.handle.net/1969.1/1130.

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The mechanism of carbon coupling reactions is traditionally represented in a very broad schematic. This thesis seeks to explore the mechanism of these reactions by focusing on Heck olefination. The Heck reaction has become a powerful tool in synthetic labs but the mechanism of this reaction has remained a topic of debate since the reaction's discovery. The catalytic cycle that has come to be accepted, while accurate in its own right, is not nearly as detailed as the complexity of the various stages of the Heck reaction suggest it should be. This study seeks to elucidate the nature of the oxidative addition of aryl halide to a palladium catalyst using a ligand that has been shown to have high activity in facilitating oxidative addition of aryl chlorides and bromides in other coupling reactions. This information is then compared to other studies in the field so that conclusions can be drawn about the oxidative addition. Also, selectivity studies seek to determine the nature of the migratory insertion of an olefin into the Pd-Ar bond. Again, comparison of results obtained in this study are compared to previous results so that a more definitive conclusion can be drawn about the oxidative addition.
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Tasker, Sarah Z. (Sarah Zinnen). "The nickel-catalyzed Mizoroki-Heck reaction : high regioselectivity in Olefin migratory insertion and photoredox-enabled indoline formation." Thesis, Massachusetts Institute of Technology, 2015. http://hdl.handle.net/1721.1/101456.

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Thesis: Ph. D. in Organic Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2015.
This electronic version was submitted by the student author. The certified thesis is available in the Institute Archives and Special Collections.
Cataloged from student-submitted PDF version of thesis. Vita
Includes bibliographical references.
[chemical formula and color illustrations ...] Achieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were able to achieve excellent selectivity for branched products (>/=19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to obtaining high branched/linear selectivity, while the appropriate base suppressed alkene isomerization of the product. Though aryl triflates are traditionally used to access the cationic Heck pathway, we have shown that by using triethylsilyl trifluoromethanesulfonate we can effect a counterion exchange of the catalytic nickel complex such that cheaper and more stable aryl chlorides, mesylates, tosylates, and sulfamates can be used to yield the same branched products with high selectivity. [chemical formula and color illustrations ...] Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C-N bond-forming reductive elimination, producing a Ni(I) complex which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multi-oxidation state nickel catalysis.
by Sarah Z. Tasker.
Ph. D. in Organic Chemistry
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Budhai, Asheena. "Migration and decarbonylation reactions of group 6 organometallic complexes using solvent-free procedures." Thesis, 2008. http://hdl.handle.net/10539/5389.

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Book chapters on the topic "Migratory-insertion reactions"

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Negishi, E. i., and T. Takahashi. "Other Migratory Insertion Reactions." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-002-00848.

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Negishi, E. i., and T. Takahashi. "Migratory Insertion Reactions of Zirconacycles with Carbon Monoxide and Isocyanides." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-002-00878.

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Negishi, E., and G. Wang. "Other Organozirconium Migratory Insertion Reactions for the Synthesis of 1,3-Dienes." In 1,3-Dienes, 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-046-00154.

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Negishi, E., and G. Wang. "Stoichiometric Synthesis of 1,3-Dienes by Metal-Mediated Coupling Reactions via Migratory Insertion." In 1,3-Dienes, 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-046-00150.

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Negishi, E., and G. Wang. "1,4-Disubstituted ,-1,3-Dienes by [2C + 2C] Alkenyl–Alkenyl Coupling via Organoboron Migratory Insertion Reactions." In 1,3-Dienes, 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-046-00151.

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Negishi, E., and G. Wang. "1,4-Disubstituted ,-1,3-Dienes by [2C + 2C] Alkynyl–Alkenyl Coupling via Organoboron Migratory Insertion Reactions." In 1,3-Dienes, 1. Georg Thieme Verlag KG, 2009. http://dx.doi.org/10.1055/sos-sd-046-00152.

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Negishi, E. i., and T. Takahashi. "C—C Bond Formation via Carbonylation and Other Migratory Insertion Reactions of Bis(η-cyclopentadienyl)monoorganozirconium Complexes." In Compounds of Groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...), 1. Georg Thieme Verlag KG, 2003. http://dx.doi.org/10.1055/sos-sd-002-00845.

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