{"title":"1.1.7 Gold/Gold Dual Catalysis","authors":"A. Hashmi","doi":"10.1055/sos-sd-231-00067","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00067","url":null,"abstract":"This chapter summarizes the reactions that have been reported that are based on dual gold catalysis. The chemistry typically involves diyne substrates, and leads to a broad range of carbo- and heterocycles. The literature up to 2019 is covered.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"11 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80260340","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":"1.1.6 Gold Dual Catalysis with Palladium, Nickel, or Rhodium","authors":"N. Patil, A. G. Tathe, V. W. Bhoyare","doi":"10.1055/sos-sd-231-00061","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00061","url":null,"abstract":"The unique intermediates accessible by exploiting the soft π-acid character of gold catalysts, make them an attractive option for dual metal catalysis reactions. Together with palladium, nickel, or rhodium, each having their own distinct character, dual catalysis with gold offers exclusive opportunities for reactivity and selectivity in installing carbon–carbon and carbon–heteroatom linkages. For instance, gold dual catalysis with palladium can be an advanced tool for cross-coupling reactions. On the other hand, unlike palladium, nickel is more readily susceptible to single-electron redox processes and hence can offer reactivity both parallel to and different from that of palladium. Another potential candidate, rhodium, is considered for dual catalysis with gold because it showcases unique reactivity such as C–H activation/transmetalation and conjugate addition. When compared to using single-metal catalyst systems, such dual-metal associations result in efficient one-pot approaches to highly regio- and stereoselective syntheses of molecules via cross couplings, cycloadditions, or rearrangements.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"18 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90037545","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":"1.2.4 Gold/Photocatalyst Dual Catalysis","authors":"L. Barriault, M. Zidan, S. Rohe","doi":"10.1055/sos-sd-231-00189","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00189","url":null,"abstract":"The use of gold catalysts in classical two-electron cross-couplings is notoriously impractical due to the high oxidation potential of gold(I)/gold(III) [e.g., E0 (AuI/AuIII) = +1.36 V]. However, when used in tandem with photocatalysts, the gold center can be oxidized one electron at a time, making cross-coupling style reactions with gold more viable. The gold(III) intermediate also has the potential to act as a Lewis acid prior to its reductive elimination step, which has spurred development of multi-bond-forming dual catalytic transformations. This dual-catalytic strategy is also applied in reactions with gold as a photocatalyst in conjunction with an organocatalyst to effectuate traditionally challenging cross couplings.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"33 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88037509","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":"1.1.4 Iridium/Zinc and Iridium/Copper Dual Catalysis","authors":"X. Huo, R. He, W. Zhang","doi":"10.1055/sos-sd-231-00041","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00041","url":null,"abstract":"Synergistic bimetallic catalysis is gaining increasing attention due to its advantages over traditional catalytic methodologies. These advantages include double activation, accurate control of reaction sites, double stereochemical control, and potential in stereodivergent synthesis. This review documents advances in the field and provides an up-to-date overview of recent developments in the use of iridium/zinc and iridium/copper catalyst systems.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"74 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72675048","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":"1.1.3 Rhodium/Palladium Dual Catalysis","authors":"U. Kim, S.-g. Lee","doi":"10.1055/sos-sd-231-00029","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00029","url":null,"abstract":"This chapter reviews the development and applications of rhodium/palladium dual catalysis in organic synthesis. Dual catalysis can be broadly classified into two types: (1) Synergistic dual catalysis, where two independent rhodium and palladium catalytic cycles operate simultaneously to activate two different starting materials with balanced kinetics to afford two catalytically activated intermediates. These activated intermediates react with each other to afford the final product. (2) Orthogonal tandem dual catalysis, where two catalytic cycles operate in a sequential manner, one after the other, to promote two or more mechanistically distinct reaction steps in a single pot to furnish the product. The first part of the chapter covers synergistic rhodium/palladium dual catalysis, detailing examples that feature a direct reaction between rhodium-activated intermediates and orthogonal, palladium-activated intermediates. The second part of the chapter describes one-pot reactions that utilize initial rhodium catalysis and sequential palladium catalysis. A single example where initial palladium catalysis is followed by subsequent rhodium catalysis is also presented.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"22 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83724785","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":"1.1.1 General Principles of Metal/Metal Dual Catalysis","authors":"Y. Nakao","doi":"10.1055/sos-sd-231-00002","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00002","url":null,"abstract":"The background and principles of dual metal/metal catalysis are briefly introduced in this section, with a particular focus on novel C–C bond-forming cross-coupling-type reactions. By taking advantage of synergistic dual metal/metal catalysis, these transformations have provided the synthetic and organometallic communities with new ideas to design challenging transformations that are difficult to catalyze using a conventional, single metal catalyst.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"78 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83770378","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":"1.2.3 Palladium/Photocatalyst Dual Catalysis","authors":"K. Muralirajan, M. Rueping","doi":"10.1055/sos-sd-231-00168","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00168","url":null,"abstract":"Palladium-catalyzed cross-coupling reactions are of great importance in chemistry. Merging palladium catalysis with photoredox catalysis has recently led to promising improvements, and typical problems associated with the use of stoichiometric oxidants, higher temperature, and harsh reaction conditions could be addressed. This chapter outlines recent developments in palladium/photoredox dual catalyzed C–C and C–N bond-formation reactions using visible-light irradiation.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"19 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77788510","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":"1.2.2 Nickel/Photocatalyst Dual Catalysis","authors":"D. Primer, G. Molander","doi":"10.1055/sos-sd-231-00100","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00100","url":null,"abstract":"This chapter outlines the broad scope of photoredox/nickel dual catalysis. Among the newer approaches to organic synthesis that engender the concept of dual catalysis, photoredox/nickel dual-catalytic cross-coupling reactions comprise one of the most rapidly developing and powerful tactics. Taken as a whole, these transformations enable novel carbon–carbon and carbon–heteroatom bond constructions that were previously challenging, if not impossible, to carry out. Most remarkably, these processes are most often carried out under near-neutral reaction conditions at ambient temperatures, with the energy to drive the reactions being provided solely by visible-light sources, thus enabling the incorporation of a broad range of diverse functional groups. As described, the development of these processes therefore provides one means to address the longstanding challenge of late-stage assembly of highly functionalized molecules via cross-coupling strategies.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"173 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79594386","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":"1.1.5 Gold/Iron Dual Catalysis","authors":"X. Shi, J. Wang","doi":"10.1055/sos-sd-231-00054","DOIUrl":"https://doi.org/10.1055/sos-sd-231-00054","url":null,"abstract":"Dual gold/iron catalysis has emerged in the past decade as a fast, efficient and economical method to access molecular complexity. Preliminary results are reviewed herein.","PeriodicalId":11383,"journal":{"name":"Dual Catalysis in Organic Synthesis 1","volume":"20 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79294404","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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