Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

Wang, Hao; Ying, Peng; Yu, Jian; Su, Weike

doi:10.6023/cjoc202009053

Cited by 12 publications

(5 citation statements)

References 146 publications

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“…Some elegant works on the construction of C–C, C–O, C–N bonds, etc. have been reported by Ito, 44–50 Bolm, 51–56 Wang, 57–60 Su, 61 Friščić 62–64 and other groups, 65–68 respectively. On the other hand, an electromagnetic mill (EMM) is a novel grinding device and uses small ferromagnetic particles as the grinding media in a rotating electromagnetic field.…”

Section: Introductionmentioning

confidence: 76%

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]

et al. 2023

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Section: Introductionmentioning

confidence: 76%

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]

et al. 2023

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“…59 However, the transformation with simple ketones has remained underdeveloped in terms of substrate scopes, stereocontrol, and redox economy. 60 In 2017, we further extended the chiral primary aminocatalysis to a synergistic tricatalytic system for asymmetric CDC involving a photoredox catalyst Ru(bpy) 3 Cl 2 , a hydrogen/electron mediator Co-(dmgH) 2 Cl 2 , and primary aminocatalyst A8 (Scheme 11). 61 The protocol could be applied to various cyclic ketones with substituted tetrahydroisoquinolines under the irradiation of visible light to afford syn-selective adducts with moderate to high diastereo-and enantioselectivity (Scheme 11, 16a−c).…”

Section: Photoredox Catalysismentioning

confidence: 99%

“…Previously, we have shown that chiral primary amine catalysts could work in concert with a photocatalyst for asymmetric α-photoalkylation. , In the past decades, catalytic asymmetric cross-dehydrogenative coupling (CDC) reactions have been explored as powerful methods for constructing C–C bonds between two unmodified C–H bonds . However, the transformation with simple ketones has remained underdeveloped in terms of substrate scopes, stereocontrol, and redox economy . In 2017, we further extended the chiral primary aminocatalysis to a synergistic tricatalytic system for asymmetric CDC involving a photoredox catalyst Ru(bpy) 3 Cl 2 , a hydrogen/electron mediator Co(dmgH) 2 Cl 2 , and primary aminocatalyst A8 (Scheme ).…”

Section: Photochemical Synergistic Catalysismentioning

confidence: 99%

Enantioselective Transformations by “1 + x” Synergistic Catalysis with Chiral Primary Amines

Cai,

Zhang,

Zhang

et al. 2024

Acc. Chem. Res.

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Metrics & MoreArticle Recommendations CONSPECTUS: Synergistic catalysis is a powerful tool that involves two or more distinctive catalytic systems to activate reaction partners simultaneously, thereby expanding the reactivity space of individual catalysis. As an established catalytic strategy, organocatalysis has found numerous applications in enantioselective transformations under rather mild conditions.Recently, the introduction of other catalytic systems has significantly expanded the reaction space of typical organocatalysis. In this regard, aminocatalysis is a prototypical example of synergistic catalysis. The combination of aminocatalyst and transition metal could be traced back to the early days of organocatalysis and has now been well explored as an enabling catalytic strategy. Particularly, the acid−base properties of aminocatalysis can be significantly expanded to include usually electrophiles generated in situ via metal-catalyzed cycles. Later on, aminocatalyst has also been exploited in synergistically combining with photochemical and electrochemical processes to facilitate redox transformations. However, synergistically combining one type of aminocatalyst with many different catalytic systems remains a great challenge. One of the most daunting challenges is the compatibility of aminocatalysts in coexistence with other catalytic species. As nucleophilic species, aminocatalysts may also bind with metal, which leads to mutual inhibition or even quenching of the individual catalytic activity. In addition, oxidative stability of aminocatalyst is also a nonneglectable issue, which causes difficulties in exploring oxidative enamine transformations.In 2007, we developed a vicinal diamine type of chiral primary aminocatalysts. This class of primary aminocatalysts was developed and evolved as functional and mechanistic mimics to the natural aldolase and has been widely applied in a number of enamine/ iminium ion-based transformations. By following a "1 + x" synergistic strategy, the chiral primary amine catalysts were found to work synergistically or cooperatively with a number of transition metal catalysts, such as Pd, Rh, Ag, Co, and Cu, or other organocatalysts, such as B(C 6 F 5 ) 3 , ketone, selenium, and iodide. Photocatalysis and electrochemical processes can also be incorporated to work together with the chiral primary amine catalysts. The 1 + x catalytic strategy enabled us to execute unexploited transformations by fine-tuning the acid−base and redox properties of the enamine intermediates and to achieve effective reaction and stereocontrol beyond the reach individually. During these efforts, an unprecedented excited-state chemistry of enamine was uncovered to make possible an effective deracemization process. In this Account, we describe our recent efforts since 2015 in exploring synergistic chiral primary amine catalysis, and the content is categorized according to the type of synergistic partner such that in each section the developed synergistic catalysis, reaction scopes, and mechanistic features...

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“…16 In many of the methods above, visible light or blue LED was applied to provide the necessary energy to overcome the endergonic reactions. 17…”

mentioning

confidence: 99%

Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C–H bonds

Zhang

Zhu

et al. 2023

Org. Chem. Front.

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Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

Cited by 12 publications

References 146 publications

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]

Enantioselective Transformations by “1 + x” Synergistic Catalysis with Chiral Primary Amines

Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C–H bonds

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Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

Cited by 12 publications

References 146 publications

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K4[Fe(CN)6]

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K4[Fe(CN)6]

Enantioselective Transformations by “1 + x” Synergistic Catalysis with Chiral Primary Amines

Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C–H bonds

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Product

Resources

About

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]

Electromagnetic mill promoted mechanochemical palladium-catalyzed solid state cyanation of aryl bromides using non-toxic K₄[Fe(CN)₆]