Recent advances in iodine mediated electrochemical oxidative cross-coupling

2018 ◽  
Vol 16 (14) ◽  
pp. 2375-2387 ◽  
Author(s):  
Kun Liu ◽  
Chunlan Song ◽  
Aiwen Lei
Keyword(s):  
Oxidative Coupling ◽  
Cross Coupling ◽  
Review Article ◽  
Coupling Reactions ◽  
Recent Advances ◽  
Oxidative Coupling Reactions

This review article gives an overview of the recent development of iodine mediated electrochemical oxidative coupling reactions.

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

2020 ◽  
Author(s):  
Ryan A. Daley ◽  
Joseph Topczewski
Keyword(s):  
Oxidative Coupling ◽  
Field Effect ◽  
Gold Catalyst ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Gold Complexes ◽  
Site Specific ◽  
Effect Parameter ◽  
Oxidative Coupling Reactions

This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). Generating an aryl nucleophile via decarboxylation obviates problems associated with transmetalation at a putative gold(III) complex. This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Furthermore, each step in a proposed mechanism was observed from isolated gold complexes, supporting a gold catalyzed mechanism.

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

2020 ◽  
Author(s):  
Ryan A. Daley ◽  
Joseph Topczewski
Keyword(s):  
Oxidative Coupling ◽  
Field Effect ◽  
Gold Catalyst ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Gold Complexes ◽  
Site Specific ◽  
Effect Parameter ◽  
Oxidative Coupling Reactions

This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). Generating an aryl nucleophile via decarboxylation obviates problems associated with transmetalation at a putative gold(III) complex. This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Furthermore, each step in a proposed mechanism was observed from isolated gold complexes, supporting a gold catalyzed mechanism.

Oxidative cross-coupling processes inspired by the Chan–Lam reaction

2021 ◽  
Vol 57 (22) ◽  
pp. 2724-2731
Author(s):  
Michael G. J. Doyle ◽  
Rylan J. Lundgren
Keyword(s):  
Carboxylic Acids ◽  
Oxidative Coupling ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Feature Article ◽  
Boronic Esters ◽  
Oxidative Coupling Reactions ◽  
Coupling Processes

This feature article describes our discovery and application of Cu-catalyzed oxidative coupling reactions of activated methylene derivatives or carboxylic acids with nucleophiles including aryl boronic esters and amines.

scholarly journals Recent Advances in Oxidative Coupling Reactions

2015 ◽  
Vol 35 (4) ◽  
pp. 743 ◽  
Author(s):  
Jian Zhang ◽  
Qingquan Lu ◽  
Chao Liu ◽  
Aiwen Lei
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reactions ◽  
Recent Advances ◽  
Oxidative Coupling Reactions

Recent Advances in Cobalt-Catalyzed Csp2 and Csp3 Cross-Couplings

Synthesis ◽  
2017 ◽  
Vol 49 (17) ◽  
pp. 3887-3894 ◽  
Author(s):  
Jeffrey Hammann ◽  
Maximilian Hofmayer ◽  
Ferdinand Lutter ◽  
Lucie Thomas ◽  
Paul Knochel
Keyword(s):  
Transition Metal ◽  
Recent Progress ◽  
Cross Coupling ◽  
Short Review ◽  
Review Article ◽  
Transition Metal Catalysis ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Cross Coupling Reactions ◽  
Recent Advances

The present short review article highlights recent progress in the field of transition-metal catalysis. An overview on recent work involving cobalt-catalyzed cross-coupling reactions and some recent advances from our laboratories are given.1 Introduction2 Csp2–Csp2 Cobalt-Catalyzed Cross-Couplings3 Csp2–Csp3 Cobalt-Catalyzed Cross-Couplings4 Conclusion

Withdrawal Notice: Recent Advances in Sonogashira Cross-Coupling Reactions Under Solvent-Free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Teng Wang ◽  
Zongrui Liu ◽  
Songlin Wang ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Editorial Policy ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Editorial Policies ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Solvent Free Conditions ◽  
Copyright Permission

The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have caused. The Bentham Editorial Policy on Article Withdrawal can be found at https://benthamscience.com/editorial-policies-main.php BENTHAM SCIENCE DISCLAIMER: It is a condition of publication that manuscripts submitted to this journal have not been published and will not be simultaneously submitted or published elsewhere. Furthermore, any data, illustration, structure or table that has been published elsewhere must be reported, and copyright permission for reproduction must be obtained. Plagiarism is strictly forbidden, and by submitting the article for publication the authors agree that the publishers have the legal right to take appropriate action against the authors, if plagiarism or fabricated information is discovered. By submitting a manuscript, the authors agree that the copyright of their article is transferred to the publishers if and when the article is accepted for publication.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

Sign in / Sign up

Export Citation Format

Share Document