Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides

Tang, Chunlin; Zhang, Ran; Zhu, Bo; Fu, Junkai; Deng, Yi; Tian, Li; Guan, Wei; Bi, Xihe

doi:10.1021/jacs.8b10874

Cited by 84 publications

(46 citation statements)

References 95 publications

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“…Benzoyl protected homoallylic amine and N-methylated picolinamide were subjected to the standard conditions, and both reactions did not occur, indicating that the pyridine N(sp 2 ) and N-H moiety were both indispensable in this transformation. It merits to mention that, the putative 8-aminoquinoline-masked 3butenoic acid, [43][44][45][46][47] which was widely used in alkene difunctionalization, did not afford any product under the optimized conditions. Substrate scope.…”

Section: Resultsmentioning

confidence: 98%

Nickel-Catalyzed Regio- and Diastereoselective Arylamination of Unactivated Alkenes

Wang

Zhang

et al. 2021

Preprint

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An intermolecular syn-1,2-arylamination of unactivated alkenes with arylboronic acids and O-benzoylhydroxylamine electrophiles has been developed with Ni(II) catalyst. The cleavable bidentate picolinamide directing group facilitated formation of stabilized 4-, 5- or 6-membered nickelacycles and enabled the difunctionalization of diverse alkenyl amines with high levels of regio-, chemo- and diastereocontrol. This general and practical protocol was compatible with broad substrate scope and high functional group tolerance. The utility of this method was further demonstrated by the site-selective late-stage modification of pharmaceutical agents.

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Section: Resultsmentioning

confidence: 98%

Nickel-Catalyzed Regio- and Diastereoselective Arylamination of Unactivated Alkenes

Wang

Zhang

et al. 2021

Preprint

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“…45 The concept of unactivated alkenes' employment in Heck-type reaction drew the attention of Fu's group, and they reported the first copper-catalyzed intermolecular Heck-type reaction of functionalized alkyl halides 53 and unactivated alkenes 54 to produce the coupled internal olefin products 55 with excellent regio-and stereoselectivity (Scheme 28). 46 In this protocol, a bidentate directing group 8-aminoquinoline (AQ) 47 was successfully employed to enhance the reactivity of non-activated olefins and control the regioselectivity. A broad substrate scope including 1°, 2°, and 3° alkyl bromides and various non-activated feedstock alkenes could be well tolerated, and the resultant internal olefin products were proven to be versatile synthetic building blocks in a variety of chemical transformations.…”

Section: Alkyl Electrophiles As Reaction Partnersmentioning

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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“…Very recently, the first regio-selective Heck reaction of alkyl bromides with unactivated aliphatic olefins was reported by Bi and co-workers (Scheme 30). 66…”

Section: Cu-catalyzed Heck-type Reactionsmentioning

confidence: 99%

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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Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides

Cited by 84 publications

References 95 publications

Nickel-Catalyzed Regio- and Diastereoselective Arylamination of Unactivated Alkenes

Nickel-Catalyzed Regio- and Diastereoselective Arylamination of Unactivated Alkenes

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

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

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