Electrochemical dehydrogenative cross-coupling of xanthenes with ketones

Yang, Yong‐Zheng; Wu, Yanchen; Song, Ren‐Jie; Li, Jin‐Heng

doi:10.1039/d0cc02580a

Cited by 55 publications

(22 citation statements)

References 78 publications

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“…On the base of previous works, 13 control experiments and CV results (see the ESI†), a possible reaction mechanism of the electrochemical C(sp 3 )–H bond arylation was proposed, and is shown in Scheme 3. First, according to the proposed mechanism, anodic oxidation of xanthene 1a took place to form the xanthene radical I , with the aid of NHPI additive.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes

et al. 2022

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“…A recent example of one pot C(sp 3 )À C(sp 3 ) dehydrogenative coupling between xanthenes and ketones has been reported by Li and collaborators (Scheme 27). [67] Xanthene derivatization has been widely investigated [68] due to their interesting biological activities and the ease at which they undergo functionalization under oxidative conditions. The latter has also proven to be valid for anodic oxidation, as we will see later in this review.…”

Section: C(sp 3 )à C Bond Formationmentioning

confidence: 99%

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update

et al. 2021

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Transition metal-catalysed processes have been widely used for the functionalization of inert CÀ H bonds. Strategies for the functionalization of the benzylic CÀ H position having a relatively weak CÀ H bond (bond dissociation energy~80-90 kcal/mol) differ from the inert aliphatic and aromatic CÀ H positions with stronger CÀ H bonds. The recent advances in the direct activation of the benzylic position through the generation of C(sp 3) radicals have demonstrated the potential of electrochemistry and photochemistry as a means for constructing new chemical bonds. This review will cover the recent progress of benzylic CÀ H functionalization through organic radical strategies employing photochemistry and electrochemistry as sustainable tools. In addition, the mechanistic details of the typical reactions have been included which, in turn, will help the researchers to look at this promising area from a different perspective towards new discoveries and often hidden opportunities. 2.1. C(sp 3)À C Bond Formation 2.2. C(sp 2)À O and C(sp 3)À O Bond Formation 2.3. C(sp 3)À N Bond Formation 2.4. C(sp 3)À S Bond Formation 2.5. C(sp 3)À Halogen Bond Formation 3. Electrochemical Benzylic C(sp 3)À H Functionalization 3.1. C(sp 3)À C Bond Formation 3.2. C(sp 3)À O Bond Formation 3.3. C(sp 3)À N Bond Formation 3.4. C(sp 3)À P Bond Formation 3.5. C(sp 3)À Halogen Bond Formation 4. Benzylic C(sp 3)À H Functionalization via Synthetic Photoelectrochemistry 5. Conclusions and Outlook

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“…The radical‐radical coupling finishes the reaction. Recently, an extension to this work describes the cross‐coupling product between xanthenes and the ketones alpha position [131] . The electrochemical synthesis of bis‐indolylmethanes ( 194 ) can be done from indoles ( 189 ) and cyclic and lineal ethers ( 190 ), through a radical chain reaction initiated in the anode by the N ‐methylindole anodic oxidation (Scheme 20b) [132] .…”

Section: C‐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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Electrochemical dehydrogenative cross-coupling of xanthenes with ketones

Abstract:
An oxidant-free electrochemical dehydrogenative cross-coupling of xanthenes and ketones for the preparation of functionalized 9-alkyl-9H-xanthenes was developed.

Cited by 55 publications

References 78 publications

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update

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

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Electrochemical dehydrogenative cross-coupling of xanthenes with ketones

Abstract: An oxidant-free electrochemical dehydrogenative cross-coupling of xanthenes and ketones for the preparation of functionalized 9-alkyl-9H-xanthenes was developed.

Cited by 55 publications

References 78 publications

Electrochemical radical C(sp3)–H arylation of xanthenes with electron-rich arenes

Electrochemical radical C(sp3)–H arylation of xanthenes with electron-rich arenes

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update

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

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Product

Resources

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Abstract:
An oxidant-free electrochemical dehydrogenative cross-coupling of xanthenes and ketones for the preparation of functionalized 9-alkyl-9H-xanthenes was developed.

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes

Electrochemical radical C(sp³)–H arylation of xanthenes with electron-rich arenes