Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides

Kwiatkowski, Megan R.; Alexanian, Erik J.

doi:10.1002/anie.201810757

Cited by 32 publications

(18 citation statements)

References 30 publications

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“…Kwiatkowski et al developed nickel-catalyzed synthetic protocol involving inactivated alkyl bromides and obtained high regioselectivity for the olefin products (Scheme 1). [8] According to their proposed mechanism, the reaction proceeded with carbocyclization followed by usual halide removal. High efficiency and selectivity of this process gives an edge over other processes in pursuing alkyl-Heck type reactions to access various target molecules of interest.…”

Section: Nickel Catalysis In the Formation Of Carbocyclementioning

confidence: 99%

Emerging Nickel Catalysis in Heck Reactions: Recent Developments

Bhakta

Ghosh

2020

Adv Synth Catal

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The synthetic application of nickel catalysts in Heck-coupling reactions is quite prominent and noticeable of late in organic synthesis. It shows great interest over the other transition metal catalysts due to its unique characteristic that prepares them more significantly applicable in different fields of synthetic application. The usefulness of nickel-catalysts relies in the fact that they are abundant in nature, relatively less precious and environment friendly. Nickel plays pivotal role in different kind of Heck reactions known such as intramolecular-, intermolecular-, reductive-Heck type reaction producing mainly carbocycles and hetero cycles of biological significance. Carbocyclization or hetero-cyclization reaction occurred under optimized reaction conditions developed and come up with the formation of various structural building blocks of naturally occurring compounds. Via reductive Heck cyclization large membered ring of carbo-or hetero-cyclic system was formed which performed key role as building blocks in pharmaceutical synthesis and bioactive molecule formation. Intermolecular Heck type reactions were comparatively more explored. Silyl-Heck, carbonyl-Heck, and other miscellaneous type reactions were covered up through nickel-catalyzed intermolecular Heck reaction. Asymmetric versions of Heck-coupling reactions are also reported to proceed even with unactivated alkenes, offering molecules having quaternary stereogenic center in a regio-and enantioselective manner. This manuscript intends to cover these entire concepts.

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Section: Nickel Catalysis In the Formation Of Carbocyclementioning

confidence: 99%

Emerging Nickel Catalysis in Heck Reactions: Recent Developments

Bhakta

Ghosh

2020

Adv Synth Catal

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“…Recently, Alexanian developed the Ni-catalyzed intramolecular and intermolecular Heck reactions of alkyl bromides 134 (Scheme 21). 51 Employing a Ni/Xantphos catalyst and Mn reductant, this reaction produced cyclized products 135a – d in good yields and enhanced alkene regioselectivity compared to the previously developed Pd-catalyzed carbocyclizations. 35 Moreover, using these conditions, an intermolecular coupling of primary and secondary alkyl bromides with electron-deficient alkenes was accomplished (products 135e – g ).…”

Section: Ni-catalyzed Heck-type Reactionsmentioning

confidence: 92%

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Kurandina¹,

Chuentragool²,

Gevorgyan

2019

Synthesis

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The Heck reaction is one of the most reliable and useful strategies for the construction of C–C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.1 Introduction2 Pd-Catalyzed Heck-Type Reactions2.1 Benzylic Electrophiles2.2 α-Carbonyl Alkyl Halides2.3 Fluoroalkyl Halides2.4 α-Functionalized Alkyl Halides2.5 Unactivated Alkyl Electrophiles3 Ni-Catalyzed Heck-Type Reactions3.1 Benzylic Electrophiles3.2 α-Carbonyl Alkyl Halides3.3 Unactivated Alkyl Halides4 Co-Catalyzed Heck-Type Reactions5 Cu-Catalyzed Heck-Type Reactions6 Other Metals in Heck-Type Reactions7 Conclusion

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“…In 2018, the group of Alexanian used nickel species as catalysis and bisphosphine compounds as ligands to realize intramolecular Heck-type reaction of a wide range of primary and secondary alkyl bromides with unactivated alkenes (Scheme 14). 26 This protocol was able to facilitate the Heck-type process in excellent yields and minimize the formation of reductive cyclization by-products. No ATRC product was observed at partial conversion, in contrast to the previously reported palladium-catalyzed carbocyclization involving auto-tandem catalysis.…”

Section: Scheme 13 Nickel-catalyzed Enantiospecific Intramolecular Hementioning

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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Nickel‐Catalyzed Mizoroki–Heck‐Type Reactions of Unactivated Alkyl Bromides

Cited by 32 publications

References 30 publications

Emerging Nickel Catalysis in Heck Reactions: Recent Developments

Emerging Nickel Catalysis in Heck Reactions: Recent Developments

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

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

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