2018
DOI: 10.1002/adsc.201801173
|View full text |Cite
|
Sign up to set email alerts
|

Substrate‐Dependent Electrochemical Dimethoxylation of Olefins

Abstract: A general and direct electrochemical dimethoxylation of olefins is reported, which enables a divergent route to different products depending on the structure of olefins. The present protocol features mild conditions and broad substrate scope (49 examples) obviating the usage of transtion-metals and external oxidants. More importantly, to rationalize the divergent route of the transformation, an ionic-like pathway involving carbocation intermediate is proposed and the diverse products is attributed to the diffe… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1
1

Citation Types

1
22
0
1

Year Published

2019
2019
2021
2021

Publication Types

Select...
8

Relationship

0
8

Authors

Journals

citations
Cited by 42 publications
(24 citation statements)
references
References 41 publications
1
22
0
1
Order By: Relevance
“…5,6 The moving contact line in a LLS system is determined not only by the interactions among the liquid molecules but also by the interactions between the liquid molecules 7 and the solid materials. [8][9][10][11] Thus, the movement of the contact line is affected by the liquid properties, the solid properties and their surface structures. 12,13 It is generally accepted that the moving contact line is controlled by the unbalanced force and the energy dissipation near the contact line.…”
Section: Introductionmentioning
confidence: 99%
“…5,6 The moving contact line in a LLS system is determined not only by the interactions among the liquid molecules but also by the interactions between the liquid molecules 7 and the solid materials. [8][9][10][11] Thus, the movement of the contact line is affected by the liquid properties, the solid properties and their surface structures. 12,13 It is generally accepted that the moving contact line is controlled by the unbalanced force and the energy dissipation near the contact line.…”
Section: Introductionmentioning
confidence: 99%
“…[2] The related electrochemical dearomative 1,2-difunctionalization of (hetero)arenes and in particular indoles has been less studied. [3][4][5][6][7][8] The dearomatization of indole, for which we have been interested for almost a decade, [9,10] generates three dimensional indolines of potential biological relevance. [11] In few cases, dearomative electrolysis could be performed from an NÀ H indole substrate [6] as it was demonstrated by Harran during the 60 gram-scale synthesis of the benzofuroindoline core of DZ-2384, a highly potent antitumoral agent inspired by the natural product diazonamide A.…”
Section: Tion; Dihydroxylation; Electrocatalystmentioning
confidence: 99%
“…[6b] However, most electrochemical methods to achieve this transformation rely on the generation of a radical cation A via the direct anodic oxidation of the indole nucleus 1 bearing an electronwithdrawing group on the nitrogen to deliver indolines 2. [7,8] According to this concept, Royer reported, in 2004, one example of the dearomative dimethoxylation of a β-tetrahydrocarboline. [7a] One example of the dimethoxylation of the 2,3-unsubstituted NÀ Ts indole was latter reported by Zhang and Xu.…”
Section: Tion; Dihydroxylation; Electrocatalystmentioning
confidence: 99%
“…Using a similar strategy to that reported by Moeller and co‐workers, in 2019, Xu and co‐workers reported lactone formation from carboxylic acid containing styrene substrates (Scheme ) . The endo ‐type cyclization in this work deserves attention.…”
Section: Ester C−o Bond Formation Through Electrolysis Of Carboxylic mentioning
confidence: 99%