ChemInform Abstract: ORGANOMETALLIC CHEMISTRY. VI. MEERWEIN REACTION. IV. MECHANISTIC ASPECTS

2015

Synlett

The intent of this account is to provide a focused overview of recent developments in aryl radical chemistry, especially extensions and applications of the Meerwein arylation and the Gomberg-Bachmann reaction. Although most of the reactions and methods described were discovered on the basis of earlier findings made by our group or logically depend on newly discovered reactivities or mechanistic principles, the rapid evolution of radical chemistry can nevertheless be traced back to the behavior of the natural product stephanosporin, which is capable of liberating 2-chloro-4-nitrophenol via an aryl radical intermediate.

Section: Syn Lettsupporting

confidence: 58%

How the Structural Elucidation of the Natural Product Stephanosporin Led to New Developments in Aryl Radical and Medicinal Chemistry

Fehler

2015

Synlett

“…The ability of diazonium salts to act as radical scavengers for nucleophilic alkyl radicals was first discovered in mechanistic studies on the Meerwein arylation [96]. Shortly after, this concept was applied for the functionalization of a limited group of activated alkenes [97][98][99].…”

Section: Carboamination Reactionsmentioning

confidence: 99%

Modern Developments in Aryl Radical Chemistry

Pratsch

Topics in Current Chemistry

2011

This review summarizes recent advances in the field of aryl radical chemistry. In particular, modern developments of the well-known Meerwein, Pschorr, and Gomberg-Bachmann reactions are presented along with new applications in natural product syntheses. Among the methods for the generation of aryl radicals, tin hydrides play a predominant role, but more and more attractive and promising alternatives are beginning to emerge.

“…by Levisalles and Rudler. 38 The formation of aryl-alkyl azo compounds as byproducts in classical copper(II) chloride mediated Meerwein arylations thereby demonstrated that diazonium ions can not only act as aryl radical sources, but also as scavengers for the alkyl radical intermediates 4 (Scheme 1). Further development of this reaction type towards a broadly applicable synthetic method was possible through the use of titanium(III) chloride 39 or iron(II) sulfate 13c,40 as reductant.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in Meerwein Arylation Chemistry

Kindt

2016

Synthesis

The Meerwein arylation has recently received much attention and a variety of new variants have been developed. Advances include new sources for aryl radicals, new radical scavengers, as well as improved reaction conditions. This short review summarizes important developments that make this radical-type reaction an even more powerful tool for the diverse functionalization of alkenes. 1 Introduction 2 Meerwein Arylations 2.