Electroorganic synthesis, 57. Synthesis of advanced prostaglandin precursors by Kolbe electrolysis, II. – Preparation of coacids and anodic initiated tandem radical‐addition / radical‐coupling reaction with (1′R,4′S,3R/S)‐3‐(cis‐4‐acetoxycyclopent ‐2‐enyloxy)‐3‐ethoxypropionic acid

Weiguny, J.; Schäfer, Hans J.

doi:10.1002/jlac.199419940303

Cited by 24 publications

(3 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Kolbe heterocoupling (Figure 1A) between two carboxylic acids -a potentially powerful Csp 3 -Csp 3 coupling method -has also been studied, albeit to a lesser extent. Such heterocouplings were historically used as a key step to synthesize prostaglandin 15,16 and jasomonic acid analogs 17 as well as a modular route to access sugar derivatives. 18 More recently, the Lam group has expanded the oxidative heterocouplings of Schaefer to accomplish vicinal olefin functionalizations.…”

Section: Main Textmentioning

confidence: 99%

Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

Zhang

Gao

Hioki

et al. 2021

Preprint

View full text Add to dashboard Cite

This work presents a modern spin on one of the oldest known Csp3–Csp3 bond forming reactions in synthetic chemistry: the Kolbe electrolysis. This reaction holds incredible promise for synthesis, yet its use has been near non-existent in mainstream organic synthesis. In contrast to the strongly oxidative electrolytic protocol employed traditionally since the 19th century, the present method utilizes in situ generated redox-active esters (RAEs) which are combined with a mildly reductive Ni-electrocatalytic cycle. It can be used to heterocouple 1o, 2o, and even certain 3o RAEs with a protocol reminiscent of amide bond formation in terms of simplicity. Due to its mild nature the reaction tolerates a range of functional groups, is scalable, and was strategically enlisted for the synthesis of 25 known compounds to reduce overall step-counts by 74%.

show abstract

Section: Main Textmentioning

confidence: 99%

Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

Zhang

Gao

Hioki

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…A different radical cyclization method for the synthesis of tetrahydrofurans and pyrrolidines was developed earlier by Schäfer and co-workers [43–45]. In their approach, unsaturated and saturated carboxylic acids were simultaneously subjected to a mixed Kolbe-type oxidation in a KOH/methanol electrolyte using an undivided cell under galvanostatic conditions (Scheme 7).…”

Section: Reviewmentioning

confidence: 99%

Recent advances in the electrochemical construction of heterocycles

Francke

2014

Beilstein J. Org. Chem.

120

View full text Add to dashboard Cite

SummaryDue to the fact that the major portion of pharmaceuticals and agrochemicals contains heterocyclic units and since the overall number of commercially used heterocyclic compounds is steadily growing, heterocyclic chemistry remains in the focus of the synthetic community. Enormous efforts have been made in the last decades in order to render the production of such compounds more selective and efficient. However, most of the conventional methods for the construction of heterocyclic cores still involve the use of strong acids or bases, the operation at elevated temperatures and/or the use of expensive catalysts and reagents. In this regard, electrosynthesis can provide a milder and more environmentally benign alternative. In fact, numerous examples for the electrochemical construction of heterocycles have been reported in recent years. These cases demonstrate that ring formation can be achieved efficiently under ambient conditions without the use of additional reagents. In order to account for the recent developments in this field, a selection of representative reactions is presented and discussed in this review.

show abstract

“…Final capture of 14 delivered 16 and 17 in a ~ 2:1 ratio and a modest 35 % overall yield (Figure 4). which leads to the synthesis of various cyclic compounds with an improved yield of 40 to 50 %, generates two new carbon-carbon bonds in a single operation (5). This methodology was extended to heterocyclic structures and successfully applied to the synthesis of a prostaglandin precursor (6).…”

Section: Introduction To Radical Cyclization Promoted By Kolbe Electr...mentioning

confidence: 99%

Studies in the Oxidation of Carboxylic Acids: New Twists for an Old Reaction. Synthesis of Various Cyclic Systems and Substituted Orthoesters

2008

View full text Add to dashboard Cite

The Kolbe reaction is probably one of the most famous reactions in organic electrochemistry and innumerable contributions have been reported since its discovery in 1834. However, many original applications of this old reaction still await to be exploited. In this Communication, we wish to describe the development of two novel methodologies based upon the Kolbe reaction and directed towards the synthesis of various cyclic systems and substituted orthoesters.

show abstract

Cited by 24 publications

References 32 publications

Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling

Recent advances in the electrochemical construction of heterocycles

Studies in the Oxidation of Carboxylic Acids: New Twists for an Old Reaction. Synthesis of Various Cyclic Systems and Substituted Orthoesters

Contact Info

Product

Resources

About