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 .