{"title":"Mass Spectrometry of Organoaluminum Derivatives","authors":"R. Stoddard, S. Collins, J. McIndoe","doi":"10.1002/9780470682531.PAT0831","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0831","url":null,"abstract":"Mass spectrometry has been applied to the characterization of organoaluminum compounds in work that dates back to the introduction of the first commercial instruments. As new ionization methods and associated instrumentation were developed, they have been applied to more difficult analyses so as to characterize the compounds of increasingly higher molecular weight, low volatility and ionic organoaluminum compounds. In thifs chapter, practical advice for performing these analyses, and choice of ionization method(s) to be applied is provided, as well as a representative survey of the various mass spectrometric techniques that have been applied to analysis of organoaluminum compounds. \u0000 \u0000 \u0000Keywords: \u0000 \u0000mass spectrometry; \u0000organoaluminum; \u0000electron ionization; \u0000chemical ionization; \u0000field desorption; \u0000electrospray ionization; \u0000fast atom bombardment; \u0000liquid secondary ion; \u0000matrix-assisted laser desorption; \u0000direct analysis in real time","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"10 1","pages":"1-15"},"PeriodicalIF":0.0,"publicationDate":"2016-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78752135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Advances in the Analytical Chemistry of Metal Phenolates","authors":"J. Zabicky","doi":"10.1002/9780470682531.PAT0854","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0854","url":null,"abstract":"","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"24 1","pages":"1-41"},"PeriodicalIF":0.0,"publicationDate":"2016-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88752298","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Advances in the Catalysis of Organic Processes by Metal Phenolates","authors":"M. Serra, D. Murtinho","doi":"10.1002/9780470682531.PAT0849","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0849","url":null,"abstract":"Transition-metal catalysts with phenolate ligands comprise a great variety of compounds with appropriate characteristics capable of promoting numerous reactions of extreme importance in synthetic organic chemistry. Included in these transformations are oxidations of alkenes, sulfides, alcohols, and alkanes, cyanations, alkynylations, alkylations, hydroaminations, and nitroaldol reactions. An extensive review of the catalysis of organic processes by metal phenolates has been presented in a previous volume of this series. This chapter is an update of the advances published from 2011 to the beginning of 2015, with emphasis on the type of reactions catalyzed by metal phenolates that have gained more attention in the literature during this period. \u0000 \u0000 \u0000Keywords: \u0000 \u0000alkylations; \u0000alkynylations; \u0000cyanations; \u0000epoxidation; \u0000hydroamination; \u0000metal phenolates; \u0000nitroaldol reactions; \u0000sulfoxidation","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"57 1","pages":"1-27"},"PeriodicalIF":0.0,"publicationDate":"2016-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87040571","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Recent Advances in the Chemistry of Metal Ynolates","authors":"M. Shindo, Kenji Matsumoto","doi":"10.1002/9780470682531.PAT0902","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0902","url":null,"abstract":"","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"94 1","pages":"1-31"},"PeriodicalIF":0.0,"publicationDate":"2016-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79614348","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"The Chemistry of Bis-Aluminated Compounds","authors":"S. Matsubara","doi":"10.1002/9780470682531.PAT0841","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0841","url":null,"abstract":"In this chapter, representative examples of bis-aluminated compound chemistry will be shown. The compounds can be classified roughly into two categories: The preparations and reactions of gem-dialuminated compounds will be discussed first, followed by those of aluminacycles. They have been expected to work as a dianion equivalent in organic syntheses, and have actually shown specific molecular transformations taking advantage of their capabilities. Although they possess a dianionic character, they have reasonable stability. As useful reactions of gem-dialuminated compounds, alkylidenation of carbonyl compounds and subsequential reactions with electrophiles will be shown. In addition, preparation of cyclic compounds via an insertion reaction of electrophiles into aluminacyles will be discussed. \u0000 \u0000 \u0000Keywords: \u0000 \u0000alkylidenation; \u0000aluminacycles; \u0000bis-aluminated compound; \u0000carbometalation; \u0000heterocycles; \u0000subsequential reaction","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"34 1","pages":"1-18"},"PeriodicalIF":0.0,"publicationDate":"2016-03-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82058674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Mass Spectrometry of Organogold Compounds","authors":"R. O'hair","doi":"10.1002/9780470682531.PAT0818","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0818","url":null,"abstract":"The use of mass spectrometry (MS) based methods in organogold chemistry is reviewed. The focus is on both fundamental gas-phase ion chemistry studies in which the mass spectrometer is used as a “gas-phase reactor” and the analytical applications of mass spectrometry. For the former, the topics covered include: thermochemical measurements (bond energies from reactions of Au+ with substrates and Au+ and R3PAu+ affinities); photoelectron, IR and UV-Vis spectroscopy; ion-molecule reactions of bare Au+, ligated Au(L)n+, Au− and gold clusters with substrates; formation and reactions of organogold ions. The latter includes a discussion on: the use of different ionization methods (electron ionization, fast-atom bombardment, electrospray ionization and matrix assisted laser desorption ionization) in the analysis of gold compounds; the use of MS in the bioinorganic chemistry of gold; MS-based studies of relevance to catalysis. \u0000 \u0000 \u0000Keywords: \u0000 \u0000bioinorganic chemistry; \u0000catalysis; \u0000electrospray ionization; \u0000gas-phase; \u0000ion-molecule reactions; \u0000mass spectrometry; \u0000organogold; \u0000spectroscopy; \u0000thermochemistry","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"69 1","pages":"1-50"},"PeriodicalIF":0.0,"publicationDate":"2015-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87387674","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alexis Archambeau, Frédéric Miege, J. Cossy, C. Meyer
{"title":"Gold-Catalyzed Reactions of Cyclopropenes","authors":"Alexis Archambeau, Frédéric Miege, J. Cossy, C. Meyer","doi":"10.1002/9780470682531.PAT0803","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0803","url":null,"abstract":"Cyclopropenes have often been used as substrates in transition metal-promoted or catalyzed reactions. Since the first reports in 2008, gold-catalyzed reactions of cyclopropenes have rapidly evolved to an active research field. The observed reactivity is essentially related to the ability of cyclopropenes to undergo ring-opening in the presence of gold(I) complexes and hence generate alkenyl gold carbenoids. These latter organogold species act as key reactive catalytic entities in a wide range of transformations including inter- or intramolecular nucleophilic additions of heteroatom or carbon nucleophiles, carbene-type coupling reactions and olefin cyclopropanations. Additionally, cyclopropenes can also behave as π nucleophiles in gold-catalyzed enyne cycloisomerizations wherein alkynes are preferentially activated by gold(I) complexes. A wide variety of acyclic and cyclic products can be produced by these gold-catalyzed reactions of cyclopropenes and the different contributions as well as the theoretical studies in this field have been summarized in this chapter. \u0000 \u0000 \u0000Keywords: \u0000 \u0000carbenoids; \u0000catalysis; \u0000cyclopropanation; \u0000cyclopropenes; \u0000gold complexes; \u0000nucleophilic additions; \u0000rearrangement; \u0000ring-opening","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"45 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2015-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86672181","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"The Chemistry of Gold–NHC Carbene Complexes","authors":"Jun Zhang, P. Gu, Kai Chen, M. Shi","doi":"10.1002/9780470682531.PAT0806","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0806","url":null,"abstract":"Au-NHC chemistry has received much attention in the last 10 years, mainly due to straightforward synthetic routes to Au(I)-NHC complexes and their catalytic interest. Now Au-NHC complexes have been employed, not only as highly selective catalysts in directed organic synthetic strategies, but also as dynamic intermediates to promote constructive chemical steps at the metal active center. Some very recent examples have described the stabilization imparted by NHC which allows to isolate otherwise “unstable” intermediates, such as vinylgold derivatives. Another important property shown by Au-NHC complexes is their luminescence. The lower energy excitation and emission bands in some Au-NHCs are of suitable wavelengths for cellular distribution studies allowing to investigate the uptake and distribution in cancer cells using fluorescence confocal microscopy. The strong Au–carbene bonds also permit stable Au-NHC complexes immune to biologically important thiol groups, and thus Au-NHCs have also been found to have potential in medicinal and biochemical applications.Keywords:gold carbene complexes;gold catalysts;luminescence;medicinal and biochemical applications;N-Heterocyclic carbene","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"31 1","pages":"1-84"},"PeriodicalIF":0.0,"publicationDate":"2015-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73325291","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Gold‐Catalyzed Hydroarylation of Alkynes","authors":"Michael E Muratore, A. Echavarren","doi":"10.1002/9780470682531.PAT0808","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0808","url":null,"abstract":"Hydroarylations, also called alkenylations of (hetero)arenes are important transformations in organic chemistry. The recent development of gold-catalyzed processes to achieve such transformations has added a new tool in the chemist's toolbox. Thus, the hydroarylations of alkynes under gold catalysis are reviewed from a mechanistic and practical point of view. Both intramolecular and the more challenging intermolecular alkenylations are considered and described in a comprehensive account that includes detailed mechanisms as well as supporting theoretical calculations when relevant. This chapter also aims at illustrating the reactivity of internal and external alkynes which may differ in certain cases, as well as the various reactivities encountered with heteroarenes and arenes. The employment of supported gold catalysts to perform this type of transformations is also discussed in the last section of the chapter. \u0000 \u0000 \u0000Keywords: \u0000 \u0000alkynes; \u0000alkenylations; \u0000catalysis; \u0000gold; \u0000hydroarylation","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"47 1","pages":"1-96"},"PeriodicalIF":0.0,"publicationDate":"2015-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83137723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Gold‐Catalyzed and Gold‐Mediated Synthesis of Heterocycles","authors":"Mie Højer Vilhelmsen, A. Hashmi","doi":"10.1002/9780470682531.PAT0800","DOIUrl":"https://doi.org/10.1002/9780470682531.PAT0800","url":null,"abstract":"This chapter will review the vast synthetic methods available in homogeneous gold catalysis towards the preparation of heterocycles. Particularly, reactions in which the gold catalyst activates a carbon-carbon multiple bond have received attention over the past three decades, but also rearrangements, cycloadditions, coupling reactions, and oxidative cyclizations have found use in the field. Each of these methodologies will be discussed through reactions in which the gold catalyst plays a central role in the cyclization by a carbon-heteroatom bond formation. Reactions in which the heterocycles are formed by a gold catalyzed carbon-carbon bond formation will not be included here. Finally, the general reaction mechanisms of the catalysis will be given and where appropriate specific reaction pathways will be reviewed. \u0000 \u0000 \u0000Keywords: \u0000 \u0000alkenes; \u0000allenes; \u0000alkynes; \u0000cycloaddition; \u0000gold catalysis; \u0000heterocycle synthesis; \u0000homogeneous catalysis; \u0000mechanism; \u0000multiple bond activation; \u0000nucleophilic addition","PeriodicalId":20036,"journal":{"name":"Patai's Chemistry of Functional Groups","volume":"99 1","pages":"1-52"},"PeriodicalIF":0.0,"publicationDate":"2015-03-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79487191","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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