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Free-Radical Synthesis and Functionalization of Heterocycles (Hardcover, 1st ed. 2018)
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Free-Radical Synthesis and Functionalization of Heterocycles (Hardcover, 1st ed. 2018)
Series: Topics in Heterocyclic Chemistry, 54
Expected to ship within 10 - 15 working days
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This volume describes the recent developments in the free-radical
mediated synthesis and elaboration of heterocycles. The first
chapter, dealing with radical cascade processes illustrates the
power and the beauty of radical chemistry with some striking
examples of total synthesis of complex natural heterocycles. As
organic chemists strive towards sustainability, radical chemistry
has recently seen major advances and efforts in this direction,
including C-H activation of arenes and unactivated alkyl groups.
Photochemical activation, for a long time the preferred mode of
activation in radical chemistry has also seen an unexpected revival
with the advent of visible light metal- and organocatalyzed
photoredox processes. A survey of these emerging areas is provided
along with the concepts at the origin of these developments. The
venerable Minisci reaction allows for direct access to
functionalized heterocycles. This process has lately seen an
interesting renaissance and is discussed in this volume. Addition
of heteroatom-centered radicals onto unsaturated systems
constitutes another powerful method to construct heterocycles.
Examples of such a strategy are proposed along with the formation
of various heterocycles relying on homolytic substitution at
sulfur, phosphorus and selenium. Additionally free-radical
functionalization of reactive functional groups including
isonitriles, isothiocyanates and related unsaturated systems which
offer a straightforward route towards useful aromatic and
non-aromatic heterocycles are discussed. Finally, as metals are
able to trigger single electron transfer both in reductive and
oxidative modes this provides another possibility for the synthesis
of heterocycles. Significant research efforts have focused on the
use of samarium, copper and other metals to access a broad variety
of heterocycles in a single pot process, starting from readily
available raw material. Examples and mechanistic insights are
discussed by experts in this area.
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