Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Peng, Fenglin; Lan, Yun; Chang, Zhihua; Wang, Chuan

doi:10.1021/jacs.9b12554

Cited by 192 publications

(88 citation statements)

References 84 publications

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“…The same group also reported a photoredox/nickel‐catalyzed asymmetric acyl‐carbamoylation reaction with aldehydes (Scheme 77a). [ 149 ] In this reaction, tetrabutylammonium decatungstate (TBADT) was used as a hydrogen atom‐transfer (HAT) photocatalyst to generate acyl radical from aldehyde. The cyclization of Ni(II) species afforded lower ee, and amide A was observed when a carbamoyl chloride without the pendant alkene was used.…”

Section: Intramolecular Dicarbofunctionalization Of Alkenes Via Cyclimentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctionalization of alkenes through a historical perspective, including intermolecular three-component reactions and intramolecular cascade reactions. Among the pathways discussed in this review, the carbometallation/cross-coupling process and the radical addition/cross-coupling process are the two major pathways for the nickel-catalyzed dicarbofunctionalization of alkenes. The oxidative cyclization and 1,2-metallate shift processes are also selectively discussed. These methods overcome the limitations associated with the reactions using noble metals in the field, providing an efficient and straightforward access to structurally diversified molecules. Yun-Cheng Luo (right) received his BSc degree in 2016 and master degree in 2019 from University of Science and Technology of China. Then he joined Professor Xingang Zhang's group at Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences to pursue his doctorate in organic chemistry. His research interests are focused on the activation of inert C-H or C-X bonds of bulky chemicals and their applications in the synthesis of fluorine-containing compounds. Chang Xu (middle) obtained his BSc degree in basic pharmacy from China Pharmaceutical University (China) in 2015. With an interest in organic chemistry and medicinal chemistry, he then began his graduate studies at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences under the supervision of Professor Xingang Zhang. His research interests are focused on the activation and transformations of fluoroalkylanes and their applications in medicinal chemistry. Xingang Zhang (left) obtained his BSc degree in 1998 from Sichuan University (China) and received the Ph.D. in 2003 at Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008, and became research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology.

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Section: Intramolecular Dicarbofunctionalization Of Alkenes Via Cyclimentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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“…Montgomery and Martin achieved similar reactivity via a C-H arylation of benzamides 372 using aryl bromides 373, although only a limited number of enantioselective examples were reported (Scheme 62c) [149]. Expansion to a system using TBADT by Wang, which is known to generate acyl radicals from aldehydes [150], allowed for the enantioselective acyl-carbamoylation of alkenes 377 with aldehydes 378 (Scheme 63) [151]. The putative mechanism in this case, based on prior work by MacMillan et al [152], proceeds via HAT from 378 to the excited state photocatalyst to generate acyl radical 378 Copper catalysis: Other metal complexes have also been used in combination with photocatalysis.…”

Section: Nickel Catalysismentioning

confidence: 99%

“…Expansion to a system using TBADT by Wang, which is known to generate acyl radicals from aldehydes [ 150 ], allowed for the enantioselective acyl-carbamoylation of alkenes 377 with aldehydes 378 ( Scheme 63 ) [ 151 ]. The putative mechanism in this case, based on prior work by MacMillan et al [ 152 ], proceeds via HAT from 378 to the excited state photocatalyst to generate acyl radical 378 • and [W] 5− H + .…”

Section: Reviewmentioning

confidence: 99%

Recent developments in enantioselective photocatalysis

Prentice¹,

Morrisson²,

Smith³

et al. 2020

Beilstein J. Org. Chem.

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Enantioselective photocatalysis has rapidly grown into a powerful tool for synthetic chemists. This review describes the various strategies for creating enantioenriched products through merging enantioselective catalysis and photocatalysis, with a focus on the most recent developments and a particular interest in the proposed mechanisms for each. With the aim of understanding the scope of each strategy, to help guide and inspire further innovation in this field.

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“…By merging hydrogen-atom-transfer photochemistry and asymmetric nickel catalysis, our group was able to use aldehydes as components in asymmetric electrophilic difunctionalizations of alkenes (Scheme 18). 27 In this case, tetrabutylammonium decatungstate (TBADT) serves as a…”

Section: Scheme 17 Nickel-catalyzed Enantioselective Electrophilic Camentioning

confidence: 99%

Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

Jin

Wang

2020

Synlett

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The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.1 Introduction2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides3 Asymmetric Electrophilic Ring-Opening Reactions4 Asymmetric Electrophilic Difunctionalization of Alkenes4.1 Two-Component Electrophilic Difunctionalization of Alkenes Involving Arylnickelation as an Enantiodetermining Step4.2 Two-Component Electrophilic Difunctionalization of Alkenes Involving Carbamoylnickelation as an Enantiodetermining Step4.3 Three-Component Electrophilic Difunctionalization of Alkenes5 Asymmetric Electrophilic Functionalization of Carbonyl Compounds6 Summary

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Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Cited by 192 publications

References 84 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Recent developments in enantioselective photocatalysis

Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

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Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Cited by 192 publications

References 84 publications

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes†

Recent developments in enantioselective photocatalysis

Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions

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Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†