Desulfonative photoredox alkylation of N -heteroaryl sulfones – an acid-free approach for substituted heteroarene synthesis

Minisci-type alkylation of electron-deficient heteroarenes has been a pivotal technique for medicinal chemists in the synthesis of drug-like molecules. However, such transformations usually require harsh conditions ( e.g. , strong acids, stoichiometric amount of oxidants, elevated temperatures, etc....

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Published inChemical science (Cambridge) Vol. 10; no. 16; pp. 4389 - 4393
Main Authors Wang, Zheng-Jun, Zheng, Shuai, Matsui, Jennifer K., Lu, Zhipeng, Molander, Gary A.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.04.2019
Royal Society of Chemistry
Subjects
Alkylation
Amines
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chemists
High temperature
Monosaccharides
Organic chemistry
Oxidizing agents
Photoredox catalysis
Physical Sciences
Science & Technology
Sulfones
FUNCTIONALIZATION
C-H ALKYLATION
CATALYSIS
NITROAROMATICS
HETEROCYCLES
ARENES
RADICALS
SINGLE-ELECTRON TRANSMETALATION
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Summary:Minisci-type alkylation of electron-deficient heteroarenes has been a pivotal technique for medicinal chemists in the synthesis of drug-like molecules. However, such transformations usually require harsh conditions ( e.g. , strong acids, stoichiometric amount of oxidants, elevated temperatures, etc. ). Herein, by utilizing photoredox catalysis, a highly-selective alkylation method using heteroaryl sulfones has been developed that can be carried out under acid-free and redox-neutral conditions. Because of these mild conditions, challenging yet privileged structures, such as monosaccharides and unprotected secondary amines, can be installed.
Bibliography:NIH RePORTER
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These authors contributed equally to this work.
ISSN:2041-6520
2041-6539
DOI:10.1039/C9SC00776H