5‐exo versus 6‐endo Thiyl‐Radical Cyclizations in Organic Synthesis

Since the discovery of the radical mediated thiol‐ene and thiol‐yne reactions, these reactions have been employed in an intramolecular manner for the synthesis of sulfur‐containing heterocycles. Although closely related on a mechanistic basis, the thiol‐ene and thiol‐yne cyclization can differ great...

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Bibliographic Details
Published in:Helvetica chimica acta 2019-11, Vol.102 (11), p.n/a
Main Authors: McCourt, Ruairí, Scanlan, Eoin M.
Format: Article
Language:English
Subjects:
Chemical synthesis
cyclization
heterocycles
radicals
Regioselectivity
Sulfur
thiolactones
thiols
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Summary:Since the discovery of the radical mediated thiol‐ene and thiol‐yne reactions, these reactions have been employed in an intramolecular manner for the synthesis of sulfur‐containing heterocycles. Although closely related on a mechanistic basis, the thiol‐ene and thiol‐yne cyclization can differ greatly in regioselectivity and product distribution, with the thiol‐ene process being more predictable and thus attracting greater utilization. Herein, we review intramolecular thiyl‐radical addition reactions and the factors leading to the observed regioselectivity in examples in which both the 5‐exo and 6‐endo mode of cyclization are feasible. We highlight the applications of these important reactions for organic synthesis in the recent literature.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201900162