Palladium‐Catalyzed Intramolecular Mizoroki‐Heck‐Type Reaction of Diarylmethyl Carbonates

Matsude, Akihiro; Hirano, Koji; Miura, Masahiro

doi:10.1002/adsc.201901398

Cited by 16 publications

(7 citation statements)

References 57 publications

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“…Miura and Hirano utilized diarylmethyl tert ‐butyl carbonates as secondary benzyl electrophiles to develop an intramolecular enantioselective Heck reaction of simple olefins, in which a kinetic resolution process was involved (Scheme 47). [ 59 ] The reaction in the presence of Pd/chiral Mandyphos ligand L27 proceeded efficiently under external base‐free conditions, affording the corresponding methyleneindane products in good yields with moderate to good enantioselecitvities. It is worth noting that this is a rare example of enantioselective Heck reaction of secondary benzyl electrophiles.…”

Section: Palladium‐catalyzed Intramolecular Asymmetric Heck Reactionsmentioning

confidence: 99%

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

2021

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Heck reaction is one of the most important carbon‐carbon bond forming reactions with wide applications in organic synthesis. Considerable advances of enantioselective Heck reaction have been achieved in the past decades. This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, which covers intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates.

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Section: Palladium‐catalyzed Intramolecular Asymmetric Heck Reactionsmentioning

confidence: 99%

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

2021

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“…[48] Cyanoselenylation via a similar pathway was also reported to access selenoenol ethers. [49] Matsude et al [50] recently demonstrated a cascade cyclization of optically active 1,1-diarylmethylcarbonates 199 via Mizoroki-Heck followed by Suzuki coupling to furnish trans-1,2disubstituted indanes 200 (Scheme 30). [50a] The oxidative addition of Pd 0 to carbonate 199 established an equilibrium between η 1 /η 3 -benzyl Pd species 199 a/199 b. Intramolecular olefin insertion followed by Suzuki coupling, generated 200 in good yields (46-99 %; 98-> 99 % es; > 20 : 1 dr).…”

Section: Electrophilic Activation/reductive Elimination Cà C Bond Formation Via Nucleopalladationmentioning

confidence: 99%

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

et al. 2021

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Dedicated to Professor S. Chandrasekaran on the occasion of his 75 th birthday.Palladium-catalyzed cascade cyclization received much attention in organic synthesis due to its efficiency and rapid transformation of simple starting materials into complex molecular skeletons. Celebrating the 10 th year of the prestigious Nobel prize for palladium chemistry, we witness it still proceeds strong over other transition metals for its versatility. Cascade reactions in contemporary organic synthesis reduced cost and time through careful design. It has emerged as the first choice, a powerful tool for multiple bond formations in one step with a wide range of functional group tolerance due to the deep understanding of various pathways. A variety of compounds with biological relevance with complex molecular scaffolds have been achieved using these cascade coupling reactions. This review outlines Pd-catalyzed cascade reactions from the post-Nobel era. Nevertheless, more discoveries and endless possibilities for new transformations are underway.

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“…Recently, Miura and co-workers achieved a palladiumcatalyzed intramolecular Heck-type reaction of diarylmethyl carbonates 7 (Scheme 7). 19 A variety of substituted indane derivatives 8 were formed in good yields under basefree, neutral conditions with only release of CO 2 and t BuOH. Moreover, the asymmetric synthesis of indane products was feasible via a Pd/optically active Mandyphos ligandmediated kinetic resolution (Scheme 7, eq.…”

Section: Scheme 6 Ligand-free Palladium-catalyzed Intramolecular Heckmentioning

confidence: 99%

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

et al. 2020

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The Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

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Palladium‐Catalyzed Intramolecular Mizoroki‐Heck‐Type Reaction of Diarylmethyl Carbonates

Cited by 16 publications

References 57 publications

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

Recent Advances of Catalytic Enantioselective Heck Reactions and Reductive‐Heck Reactions

Exploiting the Versatility of Palladium Catalysis: A Modern Toolbox for Cascade Reactions

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

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