Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 30, Pages 10934-10937Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja4050168
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Funding
- ORSAS
- EPSRC
- University of Strathclyde
- EPSRC [EP/K033077/1, EP/I501177/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K033077/1, EP/I501177/1] Funding Source: researchfish
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The prevalence of metal-based reducing reagents, including metals, metal complexes, and metal salts, has produced an empirical order of reactivity that governs our approach to chemical synthesis. However, this reactivity may be influenced by stabilization of transition states, intermediates, and products through substrate metal bonding. This article reports that in the absence of such stabilizing interactions, established chemoselectivities can be overthrown. Thus, photoactivation of the recently developed neutral organic superelectron donor 5 selectively reduces alkyl-substituted benzene rings in the presence of activated esters and nitriles, in direct contrast to metal-based reductions, opening a new perspective on reactivity. The altered outcomes arising from the organic electron donors are attributed to selective interactions between the neutral organic donors and the arene rings of the substrates.
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