Scalable Electrochemical Transition‐Metal‐Free Dehydrogenative Cross‐Coupling Amination Enabled Alkaloid Clausines Synthesis

Zhang, Pan; Li, Baoying; Niu, Lingfeng; Jia, Xiaofei; Zhang, Guoying; Liu, Siyuan; Gao, Wei; Qin, Dawei; Chen, Jianbin

doi:10.1002/adsc.202000228

Cited by 44 publications

(21 citation statements)

References 71 publications

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“…A similar transformation was developed by Chen and co‐workers [29] for the synthesis of carbazoles (Scheme 18). Unlike the previous cases, here, the substrate scope was well defined, broad, and compatible with the synthesis of a wide variety of electron‐rich and electron‐deficient carbazoles, and even dibenzofuran and thiophene‐derived carbazoles were obtained in moderate yields.…”

Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 98%

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Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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Embracing sustainable green methodologies and techniques in chemical transformations has always been in the limelight to the synthetic community. Electrosynthesis has emerged as a powerful, sustainable synthetic tool for molecular synthesis exploiting inexpensive electricity in place of sacrificial chemical oxidizing/reducing reagents. Herein, recent advances in the incorporation of transition metal‐free redox mediators in electrosynthesis for the construction of C−N bonds are outlined. Furthermore, conjugation of this strategy with flow catalysis allows easy scale up of the synthesis of molecular assembly. This comprehensive Review provides an overview of metal‐free mediated electro‐construction of C−N bonds, focusing on the reaction mechanisms involved and its synthetic applications.

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Section: Non‐metallic Redox Mediator Merged With Electrosynthesismentioning

confidence: 98%

“…Chen and co‐workers [29] reported the synthesis of various clausine alkaloids like clausine H, clausine C, clausine L, and glycozoline in good yields by utilizing their iodide‐catalyzed electrochemical methodology (Scheme 47).…”

Section: Applicationsmentioning

confidence: 99%

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

2021

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“… Chen's electrochemical reaction via N ‐centered radical. a) Electrochemical dehydrogenative cross‐coupling amination and mechanism [202] . b)Tunable electrochemical C−N vs. N−N bond formation [203] …”

Section: C‐centered Radicalsmentioning

confidence: 99%

“…Carbazole derivates ( 353 ) were prepared using the redox mediator system I − /I 2 to selectively oxidize the 2‐arylanilines ( 352 ) (Scheme 40a) [202] . The proposed mechanism describes the formation of an arylaminyl radical in a paired electrolysis using trifluoroethanol instead of HFIP.…”

Section: N‐centered Radicalsmentioning

confidence: 99%

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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During the last decade several research groups have been developing electrochemical procedures to access highly functionalized organic molecules. Among the most exciting advances, the possibility of using free radical chemistry has attracted the attention of the most important synthetic groups. Nowadays, electrochemical strategies based on these species with a synthetic purpose are published continuously in scientific journals, increasing the alternatives for the synthetic organic chemistry laboratories. Free radicals can be obtained in organic electrochemical reactions; thus, this review reassembles the last decade's (2010–2020) efforts of the electrosynthetic community to generate and take advantage of the C‐, O‐, and N‐centered radicals’ reactivity. The electrochemical reactions that occur, as well as the proposed mechanism, are discussed, trying to give clear information about the used conditions and reactivity of these reactive intermediate species.

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“…metal free conditions. [ 18‐19 ] Herein, we reported a Pd‐catalyzed electro‐oxidative intramolecular C—H amination under external oxidant‐free conditions for synthesis of carbazoles (Scheme 1).…”

Section: Background and Originality Contentmentioning

confidence: 99%

Electrochemical Palladium‐Catalyzed Intramolecular C—H Amination of 2‐Amidobiaryls for Synthesis of Carbazoles

et al. 2020

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Electrosynthesis | Palladium-catalyzed | Cross coupling | Amination | Carbazoles The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C-H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.

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Scalable Electrochemical Transition‐Metal‐Free Dehydrogenative Cross‐Coupling Amination Enabled Alkaloid Clausines Synthesis

Cited by 44 publications

References 71 publications

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Electrochemical Palladium‐Catalyzed Intramolecular C—H Amination of 2‐Amidobiaryls for Synthesis of Carbazoles

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