AI Article Synopsis
- A new method combines photochemistry and nickel mediation to create C(sp)-C(sp) bonds, using light to activate a cheap Hantzsch ester.
- The Hantzsch ester acts as both a photoreductant and a catalyst, facilitating radical generation without the need for additional photocatalysts or metal reductants.
- This technique allows for the effective coupling of various C(sp)-based radicals with (hetero)aryl bromides under mild conditions, making it suitable for sensitive compounds and drug-like structures.
Article Abstract
A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp)-C(sp) linkages is disclosed. Under light irradiation at 390 nm, commercially available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp)-centered radical architectures (including primary, secondary, stabilized benzylic, α-oxy, and α-amino systems) with (hetero)aryl bromides has been accomplished. The protocol proceeds under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179655 | PMC |
| http://dx.doi.org/10.1039/d1sc00943e | DOI Listing |
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