Journal
CHEMICAL SCIENCE
Volume 12, Issue 26, Pages 9088-9095Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc01889b
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Funding
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- National Natural Science Foundation of China [21372250, 21121062, 21302203, 20732008, 21772037, 21772226, 21861132014, 91956115]
- Shanghai Municipal Science and Technology Major Project [2018SHZDZX03]
- Fundamental Research Funds for the Central Universities [222201717003]
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The non-classical ring opening radical clock reaction using innovative NHPI esters bearing alkylidenecyclopropanes upon photoredox catalysis provides a brand-new synthetic approach for the direct preparation of a variety of alkynyl derivatives. The potential synthetic utility of this protocol is demonstrated in the diverse transformations and facile synthesis of bioactive molecules or their derivatives and medicinal substances.
Classical cyclopropylcarbinyl radical clock reactions have been widely applied to conduct mechanistic studies for probing radical processes for a long time; however, alkylidenecyclopropanes, which have a similar molecular structure to methylcyclopropanes, surprisingly have not yet attracted researcher's attention for similar ring opening radical clock processes. In recent years, photocatalytic NHPI ester activation chemistry has witnessed significant blooming developments and provided new synthetic routes for cross-coupling reactions. Herein, we wish to report a non-classical ring opening radical clock reaction using innovative NHPI esters bearing alkylidenecyclopropanes upon photoredox catalysis, providing a brand-new synthetic approach for the direct preparation of a variety of alkynyl derivatives. The potential synthetic utility of this protocol is demonstrated in the diverse transformations and facile synthesis of bioactive molecules or their derivatives and medicinal substances.
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