H-N Addition Hydroamination

A cosensitizer such as 1,3,5-triphenylbenzene or m-terphenyl can improve the reaction yields, as demonstrated in the photoamination of trans-1 -arylpropenes and 

7-methoxy-l,2-dihydronaphthalenes with ammonia. This reaction gave l-aryl-2-propylamines and 2-amino-6-methoxy-l,2,3,4-tetrahydronaphthalenes, respectively when using 1,3-dicyanobenzene as the photocatalyst [37]. Under similar conditions, the photocatalyzed nucleophilic addition of ammonia (or alkylamines) to methoxy-substituted styrene derivatives took place [38]. 

A PET reaction between excess phthalimide (in equilibrium with its conjugate base) and an alkene led to a clean phthalimidation of nonactivated double bonds. Here, the singlet excited state of phthalimide acts as the oxidant and a radical ion pair is formed. The olefin cation radical is trapped by the phthalimide anion, and back electron transfer, followed by protonation, affords the photoaddition products [40], Protected phenethylamines are readily accessible in this way. This reaction has been carried out by using NaOH as the base it has been shown that the amounts (usually equimolar with the alkene) must be carefully chosen in order to avoid the undesired competition with [2 + 2] photocycloaddition. 

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